bluuebunny/crossref_metadata_2025 huggingface dataset:
Ethynyl
p
‐Tolyl Sulfone
Authors: Waykole Liladhar , Paquette Leo A.
Published: November 2003

Ethynyl
p
‐tolyl sulfone

solvent: petroleum ether

intermediate: p‐tolyl 2‐(trimethylsilyl)ethynyl sulfone

product: Ethynyl p‐tolyl sulfone.
Reductive Annulation of Vinyl Sulfones: Bicyclo[4.3.0.]non‐1‐en‐4‐one
Authors: Lin Ho‐shen , Paquette Leo A.
Published: November 2003

Reductive annulation of vinyl sulfones: Bicyclo[4.3.0.]non‐1‐en‐4‐one

intermediate: 4‐Oxo‐1‐(phenylsulfonyl)‐cis‐bicyclo[4.3.0]non‐2‐ene.

product: Bicyclo[4.3.0]non‐1‐en‐4‐one.
Ethyl α‐(Hexahydroazepinylidene‐2)Acetate fromO‐Methylcaprolactim and Meldrum's Acid
Authors: Celerier J. P. , Deloisy‐Marchalant E. , Lhommet G. , Maitte P.
Published: November 2003

Ethyl α‐(hexahydroazepinylidene‐2)acetate fromO‐methylcaprolactim and meldrum's acid

intermediate: 71.7 g (0.30 mol) of freshly recrystallized isopropylidene α‐(hexahydroazepinylidene‐2)malonate

product: ethyl α‐(hexahydroazepinylidene‐2)acetate
3′‐Nitro‐1‐Phenylethanol by addition of Methyltriisopropoxytitanium to
m
‐Nitrobenzaldehyde
Authors: Imwinkelried René , Seebach Dieter
Published: November 2003

3′‐Nitro‐1‐Phenylethanol by addition of Methyltriisopropoxytitanium to
m
‐Nitrobenzaldehyde

product: 3′‐nitro‐1‐phenylethanol
Methyl 7‐Hydroxyhept‐5‐ynoate
Authors: Casy Guy , Patterson John W. , Taylor Richard J. K.
Published: November 2003

Methyl 7‐hydroxyhept‐5‐ynoate

intermediate: methyl 4‐bromo‐1‐butanimidate hydrochloride

intermediate: trimethyl ortho‐4‐bromobutanoate

product: methyl 7‐hydroxyhept‐5‐ynoate

byproduct: methyl 4‐(2‐propynyloxy)butanoate
3‐Hydroxy‐1‐cyclohexene‐1‐carboxaldehyde
Authors: Rigby H. L. , Neveu M. , Pauley D. , Ranu B. C. , Hudlicky T.
Published: November 2003

3‐Hydroxy‐1‐cyclohexene‐1‐carboxaldehyde

intermediate: 1‐(1,3‐Dithian‐2‐yl)‐2‐cyclohexen‐1‐ol (2)

product: 3‐Hydroxy‐1‐cyclohexene‐1‐carboxaldehyde (3)
4‐Chlorination of Electron‐Rich Benzenoid Compounds: 2,4‐Dichloromethoxybenzene
Authors: Smith John R. Lindsay , McKeer Linda C. , Taylor Jonathan M.
Published: November 2003

4‐Chlorination of electron‐rich benzenoid compounds: 2,4‐Dichloromethoxybenzene

intermediate:
N
‐chloromorpholine

product: 2,4‐dichloromethoxybenzene

byproduct: 2,6‐dichloromethoxybenzene (0.4–0.5%)

byproduct: 2,4,6‐trichloromethoxybenzene (0.4–0.6%)

product: 2‐Chloromethoxybenzene

product: 2‐Chlorophenol

product: 6‐Chloro‐2‐methylphenol

product: 4‐Chloro‐1,2‐dimethoxybenzene

product: 4‐Chloro‐3‐Methylphenol

product: 4‐Chloro‐1,3‐dimethoxybenzene

product: 4‐Chloro‐3‐methylmethoxybenzene

product: 4‐Chloro‐3,5‐dimethylphenol
Acetyltrimethylsilane
Authors: Soderquist John A.
Published: November 2003

Acetyltrimethylsilane

intermediate: 1‐(methoxyvinyl) trimethylsilane

product: acetyltrimethylsilane
3‐Butylcyclobutenone
Authors: Danheiser Rick L. , Savariar Selvaraj , Cha Don D.
Published: November 2003

3‐Butylcyclobutenone

intermediate: 3‐butyl‐4,4‐dichlorocyclobutenone

product: 3‐butylcyclobutenone
Vicinal Dicarboxylation of an Alkene:
cis
‐1‐Methylcyclopentane‐1,2‐dicarboxylic Acid
Authors: Deprés Jean‐Pierre , Greene Andrew E.
Published: November 2003

Vicinal dicarboxylation of an alkene:
cis
‐1‐methylcyclopentane‐1,2‐dicarboxylic acid

intermediate: 7,7‐dichloro‐1‐methylbicyclo[3.2.0]heptan‐6‐one

product:
cis
‐1‐methylcyclopentane‐1,2‐dicarboxylic acid
Enantioselective Oxidation of a Sulfide: (
S
)‐(−)‐Methyl
p
‐Tolyl Sulfoxide
Authors: Zhao S. H. , Samuel O. , Kagan H. B.
Published: November 2003

Enantioselective Oxidation of a Sulfide: (
S
)‐(−)‐Methyl
p
‐Tolyl Sulfoxide

reactant: 5.35 mL, 6.19 g (0.030 mol) of (S,S)‐(−)‐diethyl tartrate (DET)

catalyst: Titanium(IV) isopropoxide, Ti(OiPr)4, (4.48 mL, 0.015 mol)

reactant: Methyl p‐tolyl sulfide (4.09 mL, 4.20 g, 0.030 mol)

product: (S)‐(−)‐methyl p‐tolyl sulfoxide

product: (R)‐(+)‐methyl p‐tolyl sulfoxide

product: (S)‐(−)‐methyl phenyl sulfoxide

product: (S)‐(−)‐methyl o‐methoxyphenyl sulfoxide
Directed Homogeneous Hydrogenation: Methyl
anti
‐3‐Hydroxy‐2‐Methylpentanoate
Authors: Brown John M. , Evans Phillip L. , James Alun P.
Published: November 2003

Directed homogeneous hydrogenation: methyl
anti
‐3‐hydroxy‐2‐methylpentanoate

product: Bicyclo[2.2.1]hepta‐2,5‐diene 1,4‐bis(diphenylphosphino)butanerhodium tri‐fluoromethanesulfonate

reactant: bicyclo[2.2.1]hepta‐2,5‐diene‐2,4‐pentanedionatorhodium (117.6 mg, 0.4 mmol)

intermediate: Methyl 3‐hydroxy‐2‐methylenepentanoate.

product: methyl dl‐anti‐3‐hydroxy‐2‐methylpentanoate

product: 2R,3R‐(−)‐methyl 3‐hydroxy‐2‐methylpentanoate

byproduct: S‐(−)‐methyl 3‐hydroxy‐2‐methylenepentanoate
1,4‐Di‐
O
‐Alkyl Threitols from Tartaric Acid: 1,4‐Di‐
O
‐Benzyl‐
L
‐Threitol
Authors: Mash Eugene A. , Nelson Keith A. , Van Deusen Shawne , Hemperly Susan B.
Published: November 2003

1,4‐Di‐
O
‐alkyl threitols from tartaric acid: 1,4‐di‐
O
‐benzyl‐
L
‐threitol

intermediate: Dimethyl 2,3‐
O
‐isopropylidene‐
L
‐tartrate.

reactant:
L
‐tartaric acid (101 g, 0.673 mol)

intermediate: 2,3‐Di‐
O
‐isopropylidene‐
L
‐threitol.

intermediate: 1,4‐di‐
O
‐benzyl‐2,3‐
O
‐isopropylidene‐
L
‐threitol

product: 1,4‐Di‐
O
‐benzyl‐
L
‐threitol
Palladium‐Catalyzed Coupling of Vinyl Triflates with Organostannanes: 4‐tert‐Butyl‐1‐Vinylcyclohexene and 1‐(4‐tert‐Butylcyclohexen‐1‐yl)‐2‐Propen‐1‐one
Authors: Scott William J. , Crisp G. T. , Stille J. K.
Published: November 2003

Palladium‐catalyzed coupling of vinyl triflates with organostannanes: 4‐tert‐butyl‐1‐vinylcyclohexene and 1‐(4‐tert‐butylcyclohexen‐1‐yl)‐2‐propen‐1‐one

intermediate: 4‐tert‐Butylcyclohexen‐1‐yl trifluoromethanesulfonate

reactant: 49.5 g (0.241 mol) of 2,6‐di‐tert‐butyl‐4‐methylpyridine

reactant: 61.3 g (0.307 mol) of trimethyltin chloride

intermediate: 4.9 g of trimethylvinyltin

product: 4‐tert‐Butyl‐1‐vinylcyclohexene.

product: 1‐(4‐tert‐Butylcyclohexen‐1‐yl)‐2‐propen‐1‐one.
Intramolecular Cyclization of
cis,cis
‐1,5‐Cyclooctadiene Using Hypervalent Iodine: Bicyclo[3.3.0]octane‐2,6‐dione
Authors: Moriarty Robert M. , Duncan Michael P. , Vaid Radhe K. , Prakash Om
Published: November 2003

Intramolecular cyclization of
cis,cis
‐1,5‐cyclooctadiene using hypervalent iodine: bicyclo[3.3.0]octane‐2,6‐dione

intermediate: 2.6‐diacetoxybicyclo[3.3.0]octane

intermediate: bicyclo[3.3.0]octane‐2,6‐diol

product: bicyclo[3.3.0]octane‐2,6‐dione
(
Z
)‐4‐(Trimethylsilyl)‐3‐Buten‐1‐ol
Authors: Overman Larry E. , Brown Mark J. , McCann Stephen F.
Published: November 2003

(
Z
)‐4‐(Trimethylsilyl)‐3‐buten‐1‐ol

intermediate: 4‐(trimethylsilyl)‐3‐butyn‐1‐ol

product: (Z)‐4‐(trimethylsilyl)‐3‐buten‐1‐ol
Regioselective Synthesis of Tetrahydropyridines: 1‐(4‐Methoxyphenyl)‐1,2,5,6‐tetrahydropyridine
Authors: Overman Larry E. , Flann Chris J. , Malone Thomas C.
Published: November 2003

Regioselective synthesis of tetrahydropyridines: 1‐(4‐methoxyphenyl)‐1,2,5,6‐tetrahydropyridine

intermediate: (Z)‐4‐(trimethylsilyl)‐3‐butenyl 4‐methylbenzenesulfonate

reactant: 41.5 g (0.337 mol) of 4‐methoxyaniline

intermediate: N‐(4‐methoxyphenyl)‐(Z)‐4‐(trimethylsilyl)‐3‐butenamine

product: 1‐(4‐methoxyphenyl)‐1,2,5,6‐tetrahydropyridine
Lipase‐catalyzed kinetic resolution of alcohols via chloroacetate esters: (−)‐(1
R
,2
S
)‐
trans
‐2‐phenylcyclohexanol and (+)‐(1
S
,2
R
)‐
trans
‐2‐Phenylcyclohexanol
Authors: Schwartz A. , Madan P. , Whitesell J. K. , Lawrence R. M.
Published: November 2003

Lipase‐catalyzed kinetic resolution of alcohols via chloroacetate esters: (−)‐(1
R
,2
S
)‐
trans
‐2‐phenylcyclohexanol and (+)‐(1
S
,2
R
)‐
trans
‐2‐phenylcyclohexanol

intermediate: 100 g (0.567 mol) of racemic trans‐2‐phenylcyclohexanol

intermediate: racemic trans‐2‐phenylcyclohexyl chloroacetate

product: (−)‐(1R,2S)‐trans‐2‐phenylcyclohexanol

byproduct: (−)‐(1S,2R)‐trans‐2‐phenylcyclohexyl chloroacetate

byproduct: (−)‐(1R,2S)‐trans‐2‐phenylcyclohexanol

product: (+)‐(1S,2R)‐trans‐2‐phenylcyclohexanol
EnantioselectiveSaponification with Pig Liver Esterase (PLE): (1S,2S,3R)‐3‐Hydroxy‐2‐nitrocyclohexyl Acetate
Authors: Eberle Martin , Missbach Martin , Seebach Dieter
Published: November 2003

Enantioselective saponification with pig liver esterase (PLE): (1S,2S,3R)‐3‐hydroxy‐2‐nitrocyclohexyl acetate

intermediate: (1R,2r,3S)‐2‐Nitrocyclohexane‐1,3‐diol

intermediate: (1R,2r,3S)‐3‐Acetoxy‐2‐nitrocyclohexyl acetate

product: (1R,2r,3S)‐3‐hydroxy‐2‐nitrocyclohexyl acetate
erythro‐Directed Reduction of a β‐Keto Amide: Erythro‐1‐(3‐hydroxy‐2‐methyl‐3‐phenylpropanoyl)piperidine
Authors: Fujita M. , Hiyama T.
Published: November 2003

erythro‐Directed reduction of a β‐keto amide: erythro‐1‐(3‐hydroxy‐2‐methyl‐3‐phenylpropanoyl)piperidine

intermediate: 1‐(2‐benzoylpropanoyl)piperidine

product: erythrol‐1‐(3‐Hydroxy‐2‐methyl‐3‐phenylpropanoyl)piperidine

catalyst: tris(diethylamino)sulfonium difluorotrimethylsilicate

product: threo‐1‐(3‐Hydroxy‐2‐methyl‐3‐phenylpropanoyl)piperidine
Enol ethers by methylenation of esters: 1‐Phenoxy‐1‐Phenylethene and 3,4‐Dihydro‐2‐Methylene‐2
H
‐1‐Benzopyran
Authors: Pine Stanley H. , Kim Gia , Lee Virgil
Published: November 2003

Enol ethers by methylenation of esters: 1‐Phenoxy‐1‐Phenylethene and 3,4‐Dihydro‐2‐Methylene‐2
H
‐1‐Benzopyran

product: 1‐phenoxy‐1‐phenylethene

product: 3,4‐dihydro‐2‐methylene‐2H‐1‐benzopyran
Conversion of Esters to Allylsilanes: Trimethyl(2‐Methylene‐4‐Phenyl;3‐Butenyl)Silane
Authors: Bunnelle William H. , Narayanan B. A.
Published: November 2003

Conversion of Esters to Allylsilanes: Trimethyl(2‐Methylene‐4‐Phenyl‐3‐Butenyl)Silane

product: trimethyl(2‐methylene‐4‐phenyl‐3‐butenyl)silane

byproduct: 3‐methyl‐1‐phenyl‐1,3‐butadiene
1‐Chloro‐1‐(Trichloroethenyl)Cyclopropane
Authors: Liese Thomas , Jaekel Frank , de Meijere Armin
Published: November 2003

1‐Chloro‐1‐(trichloroethenyl)cyclopropane

solvent: 350 mL of dry tetrachloroethylene

product: 1‐chloro‐1‐(trichloroethenyl)cyclopropane
Diazo Ketone Cyclization onto a Benzene Ring: 3,4‐Dihydro‐1(2
H
)‐azulenone
Authors: Scott Lawrence T. , Sumpter Chris A.
Published: November 2003

Diazo ketone cyclization onto a benzene ring: 3,4‐Dihydro‐1(2
H
)‐azulenone

intermediate: 1‐diazo‐4‐phenyl‐2‐butanone

product: 3,4‐Dihydro‐1(2
H
)‐azulenone.
Synthesis of
N
‐Protected α‐Amino Acids from N‐(Benzyloxycarbonyl)‐
L
‐Serine via its β‐Lactone: N
α
‐(Benzyloxycarbonyl)‐β‐(Pyrazol‐1‐yl)‐
L
‐Alanine
Authors: Pansare Sunil V. , Huyer Gregory , Arnold Lee D. , Vederas John C.
Published: November 2003

Synthesis of N‐protected α‐amino acids from N‐(benzyloxycarbonyl)‐
L
‐serine via its β‐lactone: N
α
‐(benzyloxycarbonyl)‐β‐(pyrazol‐1‐yl)‐
L
‐alanine

intermediate: N‐(benzyloxycarbonyl)‐L‐serine β‐lactone

product: Nα‐(benzyloxycarbonyl)‐β‐(pyrazol‐1‐yl)‐L‐alanine

product: pyrazolylalanine
(R,R)‐1,2‐Diphenyl‐1,2‐Ethanediol (Stilbene Diol)
Authors: McKee Blaine H. , Gilheany Declan G. , Sharpless K. Barry
Published: November 2003

(R,R)‐1,2‐diphenyl‐1,2‐ethanediol (stilbene diol)

product: (R,R)‐1,2‐diphenyl‐1,2‐ethanediol (stilbene diol)
3,4‐Diethylpyrrole and 2,3,7,8,12,13,17,18‐Octaethylporphyrin
Authors: Sessler Jonathan L. , Mozaffari Azadeh , Johnson Martin R.
Published: November 2003

3,4‐Diethylpyrrole and 2,3,7,8,12,13,17,18‐octaethylporphyrin

intermediate: 3‐nitro‐4‐hexanol

intermediate: 4‐acetoxy‐3‐nitrohexane

intermediate: ethyl 3,4‐diethylpyrrole‐2‐carboxylate (3)

product: 3,4‐diethylpyrrole

product: 2,3,7,8,12,13,17,18‐octaethylporphyrin
Preparation andDiels‐Alder Reaction of a Reactive, Electron‐Deficient Heterocyclic Azadiene: Dimethyl 1,2,4,5‐Tetrazine‐3,6‐Dicarboxylate. 1,2‐Diazine (Dimethyl 4‐Phenyl‐1,2‐Diazine‐3,6‐Dicarboxylate) and Pyrrole (Dimethyl 3‐Phenylpyrrole‐2,5‐Dicarboxylate) Introduction
Authors: Boger Dale L. , Panek James S. , Patel Mona
Published: November 2003

Preparation and Diels‐Alder reaction of a reactive, electron‐deficient heterocyclic azadiene: dimethyl 1,2,4,5‐tetrazine‐3,6‐dicarboxylate. 1,2‐diazine (dimethyl 4‐phenyl‐1,2‐diazine‐3,6‐dicarboxylate) and pyrrole (dimethyl 3‐phenylpyrrole‐2,5‐dicarboxylate) introduction

intermediate: Disodium dihydro‐1,2,4,5‐tetrazine‐3,6‐dicarboxylate

intermediate: Dihydro‐1,2,4,5‐tetrazine‐3,6‐dicarboxylic acid

intermediate: Dimethyl dihydro‐1,2,4,5‐tetrazine‐3,6‐dicarboxylate

product: Dimethyl 1,2,4,5‐tetrazine‐3,6‐dicarboxylate

product: Dimethyl 4‐phenyl‐1,2‐diazine‐3,6‐dicarboxylate

product: Dimethyl 3‐phenylpyrrole‐2,5‐dicarboxylate

byproduct: methyl 3‐phenyl‐5‐carboxamidopyrrole‐2‐carboxylate
Synthesis of Furans via Rhodium(II) Acetate‐Catalyzed Reaction of Acetylenes with α‐Diazocarbonyls: Ethyl 2‐Methyl‐5‐Phenyl‐3‐Furancarboxylate
Authors: Davies Huw M. L. , Cantrell William R. , Romines Karen R. , Baum Jonathan S.
Published: November 2003

Synthesis of furans via rhodium(II) acetate‐catalyzed reaction of acetylenes with α‐diazocarbonyls: ethyl 2‐methyl‐5‐phenyl‐3‐furancarboxylate

reactant: p‐acetamidobenzenesulfonyl azide

intermediate: ethyl diazoacetoacetate

product: ethyl 2‐methyl‐5‐phenyl‐3‐furancarboxylate
Iodolactamization: 8‐exo‐Iodo‐2‐Azabicyclo[3.3.0]Octan‐3‐One
Authors: Knapp Spencer , Gibson Frank S.
Published: November 2003

Iodolactamization: 8‐exo‐iodo‐2‐azabicyclo[3.3.0]octan‐3‐one

intermediate: 2‐Cyclopentene‐1‐acetamide

intermediate: 8‐exo‐Iodo‐2‐azabicyclo[3.3.0]octan‐3‐one
4‐Benzyl‐10,19‐Diethyl‐4,10,19‐Triaza‐1,7,13,16‐Tetraoxacycloheneicosane (Triaza‐21‐Crown‐7)
Authors: Krakowiak Krzysztof E. , Bradshaw Jerald S.
Published: November 2003

4‐Benzyl‐10,19‐Diethyl‐4,10,19‐Triaza‐1,7,13,16‐Tetraoxacycloheneicosane (Triaza‐21‐Crown‐7)

intermediate: N‐[2‐(2‐Hydroxyethoxy)ethyl]acetamide

intermediate: N‐[2‐(2‐chloroethoxy)ethyl]acetamide

intermediate: 9‐benzyl‐3,9,15‐triaza‐6,12‐dioxaheptadecane

product: 4‐Benzyl‐10,19‐diethyl‐4,10,19‐triaza‐1,7,13,16‐tetraoxacycloheneicosane (triaza‐21‐crown‐7).
Tetrahydro‐3‐Benzazepin‐2‐ones by Lead Tetraacetate Oxidation of Isoquinoline Enamides: 7,8‐Dimethoxy‐1,3,4,5‐Tetrahydro‐2H‐3‐Benzazepin‐2‐one
Authors: Lenz George R. , Lessor Ralph A.
Published: November 2003

Tetrahydro‐3‐benzazepin‐2‐ones by lead tetraacetate oxidation of isoquinoline enamides: 7,8‐dimethoxy‐1,3,4,5‐tetrahydro‐2H‐3‐benzazepin‐2‐one

intermediate: 61 g (200 mmol) of N‐(tert‐butoxycarbonyl)‐6,7‐dimethoxy‐1‐methylene‐1,2,3,4‐tetrahydroisoquinoline

product: 7,8‐Dimethoxy‐1,3,4,5‐tetrahydro‐2H‐3‐benzazepin‐2‐one

intermediate: 32.1 g (100 mmol) of recrystallized N‐(tert‐butoxycarbonyl)‐7,8‐dimethoxy‐1,3,4,5‐tetrahydro‐2H‐3‐benzazepin‐2‐one

byproduct: tert‐butyl 2‐(2‐acetyl‐3,4‐dimethoxyphenyl) ethyl carbamate
2‐Substituted Pyrroles from N‐tert‐Butoxycarbonyl‐2‐Bromopyrrole: N‐tert‐Butoxycarbonyl‐2‐Trimethylsilylpyrrole
Authors: Chen Wha , Stephenson E. Kyle , Cava Michael P. , Jackson Yvette A.
Published: November 2003

2‐substituted pyrroles from N‐tert‐butoxycarbonyl‐2‐bromopyrrole: N‐tert‐butoxycarbonyl‐2‐trimethylsilylpyrrole

intermediate: N‐tert‐butoxycarbonyl‐2‐bromopyrrole (13.5 g, 54.9 mmol) in 40 mL of hexane

product: N‐tert‐butoxycarbonyl‐2‐trimethylsilylpyrrole (2)
1,2‐Addition of a Functionalized Zinc‐Copper Organometallic [
RCu
(
CN
)
Zn
I
] to an α,β‐Unsaturated Aldehyde: (E)‐2‐(4‐Hydroxy‐6‐Phenyl‐5‐Hexenyl)‐1H‐Isoindole‐1,3(2H)‐Dione
Authors: Yeh Ming Chang P. , Chen Huai Gu , Knochel Paul
Published: November 2003

1,2‐Addition of a functionalized zinc‐copper organometallic [RCu(CN)ZnI] to an α,β‐unsaturated aldehyde: (E)‐2‐(4‐hydroxy‐6‐phenyl‐5‐hexenyl)‐1H‐isoindole‐1,3(2H)‐dione

intermediate: 2‐(3‐Iodopropyl)‐1H‐isoindole‐1,3(2H)‐dione 2

reactant: 13.4 g (50 mmol) of 2‐(3‐bromopropyl)‐1H‐isoindole‐1,3(2H)‐dione 1

product: (E)‐2‐(4‐Hydroxy‐6‐phenyl‐5‐hexenyl)‐1H‐isoindole‐1,3(2H)‐dione 4
2‐Methyl‐1,3‐Cyclopentanedione
Authors: Meister Philip G. , Sivik Matthew R. , Paquette Leo A.
Published: November 2003

2‐Methyl‐1,3‐cyclopentanedione

product: 2‐methyl‐1,3‐cyclopentanedione
1‐Phenyl‐2,3,4,5‐Tetramethylphosphole
Authors: Fagan Paul J. , Nugent William A.
Published: November 2003

1‐Phenyl‐2,3,4,5‐tetramethylphosphole

product: 1‐phenyl‐2,3,4,5‐tetramethylphosphole

intermediate: (η‐C
5
H
5
)
2
ZrC
4
(CH
3
)
4
Enantioselective, Catalytic
D
iels‐
A
lder Reaction: (1S‐endo)‐3‐(Bicyclo[2.2.1]Hept‐5‐en‐2‐ylcarbonyl)‐2‐Oxazolidinone
Authors: Pikul S. , Corey E. J.
Published: November 2003

Enantioselective, catalytic Diels‐Alder reaction: (1S‐endo)‐3‐(bicyclo[2.2.1]hept‐5‐en‐2‐ylcarbonyl)‐2‐oxazolidinone

product: (1S‐endo)‐3‐(Bicyclo[2.2.1]Hept‐5‐EN‐2‐Ylcarbonyl)‐2‐Oxazolidinone

catalyst: bistriflamide of (1S,2S)‐1,2‐diphenylethylenediamine

reactant: acryloyl‐2‐oxazolidinone
Direct Degradation of the Biopolymer Poly[(R)‐3‐Hydroxybutyric Acid] to (R)‐3‐Hydroxybutanoic Acid and its Methyl Ester
Authors: Seebach Dieter , Beck Albert K. , Breitschuh Richard , Job Kurt
Published: November 2003

Direct degradation of the biopolymer poly[(R)‐3‐hydroxybutyric acid] to (R)‐3‐hydroxybutanoic acid and its methyl ester

product: (R)‐(−)‐methyl 3‐hydroxybutanoate

product: (R)‐3‐hydroxybutanoic acid
(−)‐(1S,4R)‐Camphanoyl Chloride
Authors: Gerlach Hans , Kappes Dag , Boeckman Robert K. , Maw Graham N.
Published: November 2003

(−)‐(1S,4R)‐camphanoyl chloride

intermediate: (−)‐(1R,3R)‐3‐chlorocamphoric anhydride

intermediate: (−)‐(1S,4R)‐camphanic acid

product: (−)‐(1S,4R)‐camphanoyl chloride
3‐(S)‐[(tert‐Butyldiphenylsilyl)Oxy]‐2‐Butanone
Authors: Overman Larry E. , Rishton Gilbert M.
Published: November 2003

3‐(S)‐[(tert‐butyldiphenylsilyl)oxy]‐2‐butanone

reactant: 10.0 g (84.6 mmol) of (S)‐(−)‐ethyl lactate

intermediate: ethyl 2‐(S)‐[(tert‐butyldiphenylsilyl)oxy]propanoate

product: 3‐(S)‐[(tert‐butyldiphenylsilyl)oxy]‐2‐butanone
Stereocontrolled Preparation of 3‐Acyltetrahydrofurans from Acid‐Promoted Rearrangements of Allylic Ketals: (2S,3S)‐3‐Acetyl‐8‐Carboethoxy‐2,3‐Dimethyl‐1‐Oxa‐8‐Azaspiro[4.5]Decane
Authors: Overman Larry E. , Rishton Gilbert M.
Published: November 2003

Stereocontrolled preparation of 3‐acyltetrahydrofurans from acid‐promoted rearrangements of allylic ketals: (2S,3S)‐3‐acetyl‐8‐carboethoxy‐2,3‐dimethyl‐1‐oxa‐8‐azaspiro[4.5]decane

intermediate: 10 g of a colorless oil that is comprised of the 2,3‐dimethyl‐1‐pentene‐3,4‐diols

intermediate: (2R,3S)‐ and (2S,3S)‐1,4‐dioxa‐2,3‐dimethyl‐2‐(1‐methylethenyl)‐8‐carboethoxy‐8‐azaspiro[4.5]decane

reactant: nitromethane (100 mL)

product: (2S,3S)‐3‐acetyl‐8‐carboethoxy‐2,3‐dimethyl‐1‐oxa‐8‐azaspiro[4.5]decane
Schwartz's Reagent
Authors: Buchwald Stephen L. , LaMaire Susan J. , Nielsen Ralph B. , Watson Brett T. , King Susan M.
Published: November 2003

Schwartz's reagent

product: Schwartz's Reagent
Conjugate Addition of a Vinylzirconium Reagent: 3‐(1‐Octen‐1‐yl)Cyclopentanone
Authors: Sun Ruen Chu , Okabe Masami , Coffen David L. , Schwartz Jeffrey
Published: November 2003

Conjugate addition of a vinylzirconium reagent: 3‐(1‐octen‐1‐yl)cyclopentanone

product: 3‐(1‐Octen‐1‐yl)cyclopentanone
4‐Methoxy‐4′‐Nitrobiphenyl
Authors: Stille J. K. , Echavarren Antonio M. , Williams Robert M. , Hendrix James A.
Published: November 2003

4‐Methoxy‐4′‐nitrobiphenyl

intermediate: 4‐Nitrophenyl trifluoromethanesulfonate

intermediate: Tributyl(4‐methoxyphenyl)stannane

product: 4‐Methoxy‐4′‐nitrobiphenyl

byproduct: 4,4′‐dimethoxybiphenyl

byproduct: 4‐amino‐4′‐methoxybiphenyl
2,2′‐Dimethoxy‐6‐Formylbiphenyl
Authors: Meyers Albert I. , Flanagan Mark E.
Published: November 2003

2,2′‐Dimethoxy‐6‐formylbiphenyl

intermediate: 2,3‐dimethoxybenzoyl chloride

intermediate: amido alcohol

intermediate: 2‐(2,3‐dimethoxyphenyl)‐4,4‐dimethyl‐2‐oxazoline (1)

intermediate: 2,2′‐Dimethoxy‐6‐(4″,4″‐dimethyloxazolinyl)biphenyl

product: 2,2′‐Dimethoxy‐6‐formylbiphenyl
Tributyl(3‐Methyl‐2‐Butenyl)Tin
Authors: Naruta Yoshinori , Nishigaichi Yutaka , Maruyama Kazuhiro
Published: November 2003

Tributyl(3‐methyl‐2‐butenyl)tin

product: tributyl(3‐methyl‐2‐butenyl)tin
Ubiquinone‐1
Authors: Naruta Yoshinori , Maruyama Kazuhiro
Published: November 2003

Ubiquinone‐1

product: 2,3‐dimethoxy‐5‐methyl‐6‐(3‐methyl‐2‐butenyl)‐1,4‐benzoquinone
Diastereoselective Formation of trans‐1,2‐Disubstituted Cyclohexanes from Alkylidenemalonates by an IntramolecularEne Reaction: Dimethyl (1′R,2′R,5′R)‐2‐(2′‐Isopropenyl‐5′‐Methylcyclohex‐1′‐yl)‐Propane‐1,3‐Dioate
Authors: Tietze L. F. , Beifuss U.
Published: November 2003

Diastereoselective formation of trans‐1,2‐disubstituted cyclohexanes from alkylidenemalonates by an intramolecular ene reaction: dimethyl (1′R,2′R,5′R)‐2‐(2′‐isopropenyl‐5′‐methylcyclohex‐1′‐yl)‐propane‐1,3‐dioate

intermediate: Methyl (5R)‐2‐(methoxycarbonyl)‐5,9‐dimethyldeca‐2,8‐dienoate, 3

product: Dimethyl (1′R,2′R,5′R)‐2‐(2′‐isopropenyl‐5′‐methylcyclohex‐1′‐yl)propane‐1,3‐dioate, 4a
Methoxycarbonylmethylation of Aldehydes via Siloxycyclopropanes: Methyl 3,3‐Dimethyl‐4‐Oxobutanoate
Authors: Reissig Hans‐Ulrich , Reichelt Ingrid , Kunz Thomas
Published: November 2003

Methoxycarbonylmethylation of aldehydes via siloxycyclopropanes: methyl 3,3‐dimethyl‐4‐oxobutanoate

intermediate: 2‐methyl‐1‐(trimethylsiloxy)propene

intermediate: methyl 2,2‐dimethyl‐3‐(trimethylsiloxy)‐1‐cyclopropanecarboxylate

reactant: 24.0 g (240 mmol) of methyl diazoacetate

product: methyl 3,3‐dimethyl‐4‐oxobutanoate
Titanium‐Mediated Addition of Silyl Dienol Ethers to Electrophilic Glycine: 4‐Ketopipecolic Acid Hydrochloride
Authors: Mühlemann Clarisse , Hartmann Peter , Obrecht Jean‐Pierre
Published: November 2003

Titanium‐mediated addition of silyl dienol ethers to electrophilic glycine: 4‐ketopipecolic acid hydrochloride

intermediate: tert‐Butyl [1‐(tert‐butoxycarbonyl)‐3‐oxo‐4‐pentenyl]carbamate

product: 4‐Ketopipecolic acid hydrochloride

reactant: Tetraethyl orthotitanate, 22.9 g (0.100 mol), (Fluka Chemical Corporation

reactant: Titanium chloride (TiCl4) (Fluka Chemical Corporation), 19.0 g (0.100 mol
Dialkyl Mesoxalates by Ozonolysis of Dialkyl Benzalmalonates: Dimethyl Mesoxalate
Authors: Tietze Lutz F. , Bratz Matthias
Published: November 2003

Dialkyl mesoxalates by ozonolysis of dialkyl benzalmalonates: dimethyl mesoxalate

product: dimethyl mesoxalate hydrate
L
‐(S)‐Glyceraldehyde Acetonide
Authors: Hubschwerlen Christian , Specklin Jean‐Luc , Higelin J.
Published: November 2003

L
‐(S)‐glyceraldehyde acetonide

product: L‐(S)‐glyceraldehyde acetonide
(R)‐(+)‐2‐Hydroxy‐1,2,2‐Triphenylethyl Acetate
Authors: Braun Manfred , Gräf Silke , Herzog Sabine
Published: November 2003

(R)‐(+)‐2‐hydroxy‐1,2,2‐triphenylethyl acetate

intermediate: (R)‐(+)‐1,1,2‐Triphenylethanediol

product: (R)‐(+)‐2‐Hydroxy‐1,2,2‐triphenylethyl acetate [(R)‐HYTRA]

reactant: methyl (R)‐(−)‐mandelate

reactant: (R)‐(−)‐mandelic acid (BASF AG, D‐Ludwigshafen)
Benzocyclobutenone by Flash Vacuum Pyrolysis
Authors: Schiess Peter , Barve Ppatibha V. , Dussy Franz E. , Pfiffner Andreas
Published: November 2003

Benzocyclobutenone by flash vacuum pyrolysis

reactant: 2‐toluic acid chloride (240 g, 1.55 mol)

product: Benzocyclobutenone

byproduct: benzyl chloride

reactant: 106 g of almost colorless 2‐toluic acid
Generation of N,N‐Diethylcarbamoyllithium Via Lithium‐Tellurium Exchange and its Reaction with 3‐Phenylpropanal: N,N‐Diethyl‐2‐Hydroxy‐4‐Phenylbutanamide
Authors: Kambe Nobuaki , Inoue Toru , Sonoda Noboru
Published: November 2003

Generation of N,N‐diethylcarbamoyllithium via lithium‐tellurium exchange and its reaction with 3‐phenylpropanal: N,N‐diethyl‐2‐hydroxy‐4‐phenylbutanamide

reactant: Finely ground elemental tellurium (13.40 g, 105 mmol)

byproduct: dibutyl telluride

product: N,N‐diethyl‐2‐hydroxy‐4‐phenylbutanamide

product: N,N‐diethylphenylglyoxylamide [Et
2
NC(O)C(O)Ph]
1,3‐Diols from Lithium β‐Lithioalkoxides Generated by the Reductive Lithiation of Epoxides: 2,5‐Dimethyl‐2,4‐Hexanediol
Authors: Mudryk Boguslaw , Cohen Theodore
Published: November 2003

1,3‐Diols from lithium β‐lithioalkoxides generated by the reductive lithiation of epoxides: 2,5‐dimethyl‐2,4‐hexanediol

product: 2,5‐Dimethyl‐2,4‐hexanediol

product: 5‐methyl‐2,4‐hexanediol

product: 1‐p‐anisyl‐1,3‐butanediol

product: 2‐(1‐hydroxy‐2‐methylpropyl)cyclohexanol
Spiroannelation of Enol Silanes: 2‐Oxo‐5‐Methoxysplro[5.4]Decane
Authors: Lee Thomas V. , Porter John R.
Published: November 2003

Spiroannelation of enol silanes: 2‐oxo‐5‐methoxysplro[5.4]decane

intermediate: 1‐bromo‐3,3‐dimethoxypropane

solvent: petroleum ether (10 mL)

intermediate: 1‐trimethylstannyl‐3,3‐dimethoxypropane

reactant: trimethylsilyl trifluoromethanesulfonate (1.47 g; 6.6 mmol)

catalyst: titanium tetrachloride (7.40 g, 39.0 mmol) in dichloromethane (10 mL)

product: 2‐oxo‐5‐methoxyspiro[5.4]decane

reactant: Cyclohexane carboxaldehyde was obtained from the Aldrich Chemical Company, Inc.
1‐Trifluoromethyl‐1‐Cyclohexanol
Authors: Ramaiah Pichika , Krishnamurti Ramesh , Prakash G. K. Surya
Published: November 2003

1‐Trifluoromethyl‐1‐cyclohexanol

reactant: bromotrifluoromethane

intermediate: (trifluoromethyl)trimethylsilane

product: 1‐trifluoromethyl‐1‐cyclohexanol
Diethyl 1‐Propyl‐2‐Oxoethylphosphonate
Authors: Savignac Philippe , Patois Carl
Published: November 2003

Diethyl 1‐propyl‐2‐oxoethylphosphonate

product: diethyl 1‐propyl‐2‐oxoethylphosphonate
Conversion of Amines to Phospho Esters: Decyl Diethyl Phosphate
Authors: Nikolaides Nick , Schipor Ioanna , Ganem Bruce
Published: November 2003

Conversion of amines to phospho esters: decyl diethyl phosphate

reactant: 10.0 mL (0.05 mol) of decylamine

solvent: 35 mL (0.25 mol) of triethylamine

reactant: 7.4 mL (0.05 mol) of diethyl chlorophosphate

product: Decyl diethyl phosphate.

intermediate: 14 g (0.048 mol) of diethyl decylphosphoramidate

byproduct: decyl isoamyl ether
2,2′‐Bi‐5,6‐Dihydro‐1,3‐Dithiolo[4,5‐b][1,4]Dithiinylidene (BEDT‐TTF)
Authors: Larsen Jan , Lenoir Christine
Published: November 2003

2,2′‐bi‐5,6‐dihydro‐1,3‐dithiolo[4,5‐b][1,4]dithiinylidene (BEDT‐TTF)

intermediate: 2‐oxo‐1,4‐dithiane

intermediate: 3‐Chloro‐2‐oxo‐1,4‐dithiane

reactant: potassium O‐(2‐propyl) dithiocarbonate (13.1 g, 0.075 mol)

intermediate: 2‐Oxo‐3‐(2‐propoxythiocarbonylthio)‐1,4‐dithiane

intermediate: 2‐oxo‐5,6‐dihydro‐1,3‐dithiolo[4,5b][1,4]dithiin

product: 2,2′‐Bi‐5,6‐dihydro‐1,3‐dithiolo[4,5‐b][1,4]dithiinylidene(BEDT‐TTF)
Alkylidenation of Ester Carbonyl Groups: (Z)‐1‐Ethoxy‐1‐Phenyl‐1‐Hexene
Authors: Takai Kazuhiko , Kataoka Yasutaka , Miyai Jiro , Okazoe Takashi , Oshima Koichiro , Utimoto Kiitiro
Published: November 2003

Alkylidenation of ester carbonyl groups: (Z)‐1‐ethoxy‐1‐phenyl‐1‐hexene

reactant: 20 g (0.20 mol) of dry diisopropylamine

reactant: 15 mL (38 g, 0.22 mol) of dibromomethane

reactant: 22 mL (37 g, 0.20 mol) of 1‐iodobutane

reactant: 120 mL of hexamethylphosphoric triamide

reactant: 1,1‐dibromopentane

catalyst: 140 mL (0.28 mol) of a 2.0 M solution of titanium tetrachloride

solvent: 84 mL (0.56 mol) of tetramethylethylenediamine

catalyst: 0.88 g (3.2 mmol) of lead (II) chloride

product: 93:7 mixture of (Z)‐ and (E)‐1‐ethoxy‐1‐phenyl‐1‐hexene
A Simple and Convenient Method for the Oxidation of Organoboranes Using Sodium Perborate: (+)‐Isopinocampheol
Authors: Kabalka George W. , Maddox John T. , Shoup Timothy , Bowers Karla R.
Published: November 2003

A Simple and convenient method for the oxidation of organoboranes using sodium perborate: (+)‐isopinocampheol

intermediate: (+)‐Diisopinocampheylborane

intermediate: (+)‐Isopinocampheol

reactant: (1S)‐(−)‐α‐Pinene [99%, 98% optical purity, [α]25D −50.6° neat] was purchased from Aldrich Chemical Company, Inc.
Double Hydroxylation Reaction for Construction of the Corticoid Side Chain: 16α‐Methylcortexolone
Authors: Horiguchi Yoshiaki , Nakamura Eiichi , Kuwajima Isao
Published: November 2003

Double hydroxylation reaction for construction of the corticoid side chain: 16α‐methylcortexolone

intermediate: (Z)‐16α‐methyl‐20‐trimethylsiloxy‐4,17(20)‐pregnadien‐3‐one

product: 16α‐Methylcortexolone
(+)‐(2R,8aR*)‐[(8,8‐Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)‐(2R,8aR*)‐[(8,8‐Dichlorocamphoryl)Sulfonyl]Oxaziridine
Authors: Chen Bang‐Chi , Murphy Christopher K. , Kumar Anil , Reddy R. Thimma , Clark Charles , Zhou Ping , Lewis Bryan M. , Gala Dinesh , Mergelsberg Ingrid , Scherer Dominik , Buckley Joseph , DiBenedetto Donald , Davis Franklin A.
Published: November 2003

(+)‐(2R,8aR*)‐[(8,8‐Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)‐(2R,8aR*)‐[(8,8‐Dichlorocamphoryl)Sulfonyl]Oxaziridine

intermediate: (−)‐(3‐oxocamphorylsulfonyl)imine

intermediate: (+)‐(7,7‐dimethoxy camphorylsulfonyl)imine

intermediate: (+)‐(7,7‐dichlorocamphorylsulfonyl)imine

product: (+)‐(2R,8aR*)‐[(8,8‐dimethoxycamphoryl)sulfonyl]oxaziridine (1)

product: (−)‐(2S,8aR*)‐[(8,8‐dimethoxycamphoryl)sulfonyl]oxaziridine

product: (+)‐(2R,8aR*)‐[(8,8‐dichlorocamphoryl)sulfonyl] oxaziridine (2)

product: (−)‐(2S,8aR*)‐[(8,8‐dichlorocamphoryl)sulfonyl]oxaziridine
Asymmetric Synthesis of trans‐2‐Aminocyclohexanecarboxylic Acid Derivatives from Pyrrolobenzodiazepine‐5,11‐diones: (1S,2S)‐2‐(N‐Tosylamino)Cyclohexanecarboxylic Acid
Authors: Schultz Arthur G. , Alva Carlos W.
Published: November 2003

Asymmetric synthesis of trans‐2‐aminocyclohexanecarboxylic acid derivatives from pyrrolobenzodiazepine‐5,11‐diones: (1S,2S)‐2‐(N‐tosylamino)cyclohexanecarboxylic acid

intermediate: (5aS,9aS,11aS)‐Perhydro‐5H‐pyrrolo[2,1‐c][1,4]benzodiazepine‐5,11‐dione

intermediate: (1S,2S)‐2‐(N‐Tosylamino)‐1‐[((2S)‐2‐carbomethoxypyrrolidinyl)carbonyl] cyclohexane

product: (1S,2S)‐2‐(N‐Tosylamino)cyclohexanecarboxylic acid
Diethyl (2S,3R)‐2‐(N‐tert‐butoxycarbonyl)amino‐ 3‐Hydroxysuccinate
Authors: Saito Seiki , Komada Kanji , Moriwake Toshio
Published: November 2003

Diethyl (2S,3R)‐2‐(N‐tert‐butoxycarbonyl)amino‐ 3‐hydroxysuccinate

intermediate: diethyl (2S,3S)‐2‐bromo‐3‐hydroxysuccinate

intermediate: diethyl (2R,3R)‐2,3‐epoxysuccinate (3)

intermediate: diethyl (2S,3R)‐2‐azido‐3‐hydroxysuccinate (4)

product: diethyl (2S,3R)‐2‐(N‐tert‐butoxycarbonyl)amino‐3‐hydroxysuccinate (5)
Enantiomerically Pure β‐Amino Acids from 2‐
tert
‐Butyl‐1‐Carbomethoxy‐2,3‐Dihydro‐4(1H)‐Pyrimidinone: (R)‐3‐Amino‐3‐(p‐Methoxyphenyl)Propionic Acid
Authors: Lakner F. J. , Chu K. S. , Negrete G. R. , Konopelski J. P.
Published: November 2003

Enantiomerically pure β‐amino acids from 2‐
tert
‐butyl‐1‐carbomethoxy‐2,3‐dihydro‐4(1H)‐pyrimidinone: (R)‐3‐amino‐3‐(p‐methoxyphenyl)propionic acid

intermediate: (S,S)‐2‐tert‐Butyl‐1‐carbomethoxy‐6‐carboxy‐2,3,5,6‐tetrahydro‐4(1H)‐pyrimidinone, 1

intermediate: (S)‐2‐tert‐Butyl‐1‐carbomethoxy‐2,3‐dihydro‐4(1H)‐pyrimidinone, 3

intermediate: 2 as a clear, colorless syrup

intermediate: (R)‐2‐tert‐Butyl‐6‐(4‐methoxyphenyl)‐5,6‐dihydro‐4(1H)‐pyrimidinone

product: (R)‐3‐Amino‐3‐(p‐methoxyphenyl)propionic acid

intermediate: acyl aminal
2‐Cyclohexene‐1,4‐Dione
Authors: Oda Masaji , Kawase Takeshi , Okada Tomoaki , Enomoto Tetsuya
Published: November 2003

2‐cyclohexene‐1,4‐dione

intermediate: endo‐Tricyclo[6.2.1.02,7]undeca‐4,9‐diene‐3,6‐dione 1.

intermediate: endo‐Tricyclo[6.2.1.02,7]undec‐9‐ene‐3,6‐dione 2.

product: 2‐cyclohexene‐1,4‐dione 3
Conversion of Methyl Ketones into Terminal Acetylenes: Ethynylferrocene
Authors: Polin Johann , Schottenberger Herwig
Published: November 2003

Conversion of methyl ketones into terminal acetylenes: Ethynylferrocene

reactant: 22.8 g (0.1 mol) of acetylferrocene

solvent: 25 mL (0.32 mol) of N,N‐dimethylformamide (DMF)

reactant: 25 mL (0.27 mol) of phosphorus oxychloride

intermediate: (2‐formyl‐1‐chlorovinyl)ferrocene

solvent: 300 mL of anhydrous 1,4‐dioxane

product: ethynylferrocene
4,5‐Dibenzoyl‐1,3‐Dithiole‐2‐Thione
Authors: Hansen Thomas K. , Becher Jan , Jørgensen Tine , Varma K. Sukumar , Khedekar Rajesh , Cava Michael P.
Published: November 2003

4,5‐dibenzoyl‐1,3‐dithiole‐2‐thione

product: 4,5‐Dibenzoylthio‐1,3‐dithiole‐2‐thione (3)

intermediate: 16 g (0.0223 mol) of tetraethylammonium bis(1,3‐dithiole‐2‐thione‐4,5‐dithio) zincate (2)
Acetylenic Ethers From Alcohols and Their Reduction to
Z
‐ and
E
‐Enol Ethers: Preparation of 1‐Menthoxy‐1‐Butyne from Menthol and Conversion to (Z)‐ and (E)‐1‐Menthoxy‐1‐Butene
Authors: Kann Nina , Bernardes Vania , Greene Andrew E.
Published: November 2003

Acetylenic ethers from alcohols and their reduction to Z‐ and E‐enol ethers: Preparation of 1‐menthoxy‐1‐butyne from menthol and conversion to (Z)‐ and (E)‐1‐menthoxy‐1‐butene

product: 1‐Menthoxy‐1‐butyne

product: (Z)‐1‐Menthoxy‐1‐butene

product: (E)‐1‐Menthoxy‐1‐butene

byproduct: menthoxyacetylene

product: adamantyloxyacetylene
Pyridine‐Derived Triflating Reagents: N‐(2‐Pyridyl)‐Triflimide and N‐(5‐Chloro‐2‐Pyridyl)Triflimide
Authors: Comins Daniel L. , Dehghani Ali , Foti Christopher J. , Joseph Sajan P.
Published: November 2003

Pyridine‐derived triflating reagents: N‐(2‐pyridyl)‐triflimide and N‐(5‐chloro‐2‐pyridyl)triflimide

product: N‐(2‐pyridyl)triflimide

product: N‐(5‐chloro‐2‐pyridyl)triflimide
Bis(Trimethylsilyl) Peroxide (BTMSPO)
Authors: Dembech P. , Ricci A. , Seconi G. , Taddei M.
Published: November 2003

Bis(trimethylsilyl) peroxide (BTMSPO)

intermediate: Diazabicyclooctane‐hydrogen peroxide (DABCO · 2H2O2) complex

product: Bis(trimethylsilyl) peroxide (BTMSPO)
Synthesis of Epoxides Using Dimethyldioxirane: trans‐Stilbene Oxide
Authors: Murray Robert W. , Singh Megh
Published: November 2003

Synthesis of epoxides using dimethyldioxirane: trans‐stilbene oxide

intermediate: Dimethyldioxirane

product: trans‐Stilbene oxide
Nitroacetaldehyde Diethyl Acetal
Authors: Jäger V. , Poggendorf P.
Published: November 2003

Nitroacetaldehyde diethyl acetal

reactant: 180 g (2.95 mol) of nitromethane

product: nitroacetaldehyde diethyl acetal 1
Rhodium‐Catalyzed Heterocycloaddition of a Diazomalonate and a Nitrile: 4‐Carbomethoxy‐5‐Methoxy‐2‐Phenyl‐1,3‐Oxazole
Authors: Tullis Joshua S. , Helquist Paul
Published: November 2003

Rhodium‐catalyzed heterocycloaddition of a diazomalonate and a nitrile: 4‐carbomethoxy‐5‐methoxy‐2‐phenyl‐1,3‐oxazole

intermediate: dimethyl diazomalonate

product: 4‐carbomethoxy‐5‐methoxy‐2‐phenyl‐1,3‐oxazole

reactant: diazo formylacetate (2)
Catalytic Asymmetric Allylation Reactions:(S)‐1‐(Phenylmethoxy)‐4‐Penten‐2‐ol
Authors: Keck Gary E. , Krishnamurthy Dhileepkumar
Published: November 2003

Catalytic asymmetric allylation reactions:(S)‐1‐(phenylmethoxy)‐4‐penten‐2‐ol

catalyst: (S)‐(−)‐1,1′‐bi‐2‐naphthol [(S)‐BINOL] (1.14 g, 4.0 mmol)

product: (S)‐1‐(phenylmethoxy)‐4‐penten‐2‐ol
Ethyl Glycidate from (S)‐Serine: Ethyl (R)‐(+)‐2,3‐Epoxypropanoate
Authors: Petit Y. , Larchevêque M.
Published: November 2003

Ethyl glycidate from (S)‐serine: Ethyl (R)‐(+)‐2,3‐epoxypropanoate

intermediate: potassium glycidate

product: ethyl glycidate

intermediate: (S)‐(−)‐2‐Bromo‐3‐hydroxypropanoic acid

product: Methyl 2,3‐epoxypropanoate
(4R,5S)‐4,5‐Diphenyl‐3‐Vinyl‐2‐Oxazolidinone
Authors: Akiba T. , Tamura O. , Terashima S.
Published: November 2003

(4R,5S)‐4,5‐diphenyl‐3‐vinyl‐2‐oxazolidinone

intermediate: (4R,5S)‐4,5‐diphenyl‐2‐oxazolidinone

intermediate: (4R,5S)‐3‐(Methoxyethyl)‐4,5‐diphenyl‐2‐oxazolidinone

product: (4S,5R)‐4,5‐diphenyl‐3‐vinyl‐2‐oxazolidinone
Synthesis of Chiral (E)‐Crotylsilanes: [3R‐ and 3S‐]‐(4E)‐Methyl 3‐(Dimethylphenylsilyl)‐4‐Hexenoate
Authors: Beresis Richard T. , Solomon Jason S. , Yang Michael G. , Jain Nareshkumar F. , Panek James S.
Published: November 2003

Synthesis of chiral (E)‐crotylsilanes: [3R‐ and 3S‐]‐(4E)‐methyl 3‐(dimethylphenylsilyl)‐4‐hexenoate

intermediate: (±)‐1‐(Dimethylphenylsilyl)‐1‐buten‐3‐ol (2a)

catalyst: 12 mg (2.05 × 10−5 mol) of bis(η‐divinyltetramethyldisiloxane)tri‐tert‐butylphosphineplatinum(0)

intermediate: (3S)‐1‐(Dimethylphenylsilyl)‐1‐buten‐3‐ol (3a)

intermediate: (3R)‐1‐(dimethylphenylsilyl)‐1‐buten‐3‐ol acetate (3b)

intermediate: (3R)‐1‐(Dimethylphenylsilyl)‐1‐buten‐3‐ol (3c)

product: (3S, 4E)‐Methyl 3‐(dimethylphenylsilyl)‐4‐hexenoate (4a)
Synthesis of β‐Lactones by Aldolization of Ketones with Phenyl Ester Enolates:3,3‐Dimethyl‐1‐Oxaspiro[3.5]Nonan‐2‐One
Authors: Wedler Christine , Schick Hans
Published: November 2003

Synthesis of β‐lactones by aldolization of ketones with phenyl ester enolates: 3,3‐dimethyl‐1‐oxaspiro[3.5]nonan‐2‐one

reactant: phenyl 2‐methylpropanoate (27.09 g, 0.165 mol) in THF (50 mL)

product: 3,3‐dimethyl‐1‐oxaspiro[3.5]nonan‐2‐one

product: (±)‐3‐ethyl‐1‐oxaspiro[3.5]nonan‐2‐one

product: (3R*,4R*)‐ and (3R*,4S*)‐4‐isopropyl‐4‐methyl‐3‐octyl‐2‐oxetanone
Photoinduced‐Addition of Methanol to (5S)‐(5‐O‐tert‐Butyldimethylsiloxymethyl)Furan‐2(5H)‐One: (4R,5S)‐4‐Hydroxymethyl‐(5‐O‐tert‐Butyldimethylsiloxymethyl)Furan‐2(5H)‐One
Authors: Mann John , Weymouth‐Wilson Alexander C.
Published: November 2003

Photoinduced‐addition of methanol to (5S)‐(5‐O‐tert‐butyldimethylsiloxymethyl)furan‐2(5H)‐one: (4R,5S)‐4‐hydroxymethyl‐(5‐O‐tert‐butyldimethylsiloxymethyl)furan‐2(5H)‐one

intermediate: methyl (4S)‐4,5‐O‐isopropylidenepent‐(2Z)‐enoate

intermediate: (S)‐5‐hydroxymethylfuran‐2(5H)‐one

intermediate: (5S)‐(5‐O‐tert‐butyldimethylsiloxymethyl)furan‐2(5H)‐one

product: (4R,5S)‐4‐Hydroxymethyl‐(5‐O‐tert‐butyldimethylsiloxymethyl)furan‐2(5H)‐one

reactant: 23.7 g (0.13 mol) of benzophenone

byproduct: benzpinacol

byproduct: (4R,5S)‐4‐diphenylhydroxymethyl‐5‐tert‐butyldimethylsiloxymethylfuran‐2(5H)‐one
Wittig Olefination of Perfluoroalkyl Carboxylic Esters; Synthesis of 1,1,1‐Trifluoro‐2‐Ethoxy‐5‐Phenylpent‐2‐Ene and 1‐Perfluoroalkyl Epoxy Ethers: 1,1,1‐Trifluoro‐2‐Ethoxy‐2,3‐Epoxy‐5‐Phenylpentane
Authors: Bégué Jean‐Pierre , Bonnet‐Delpon Danièle , Kornilov Andrei
Published: November 2003

Wittig olefination of perfluoroalkyl carboxylic esters; synthesis of 1,1,1‐trifluoro‐2‐ethoxy‐5‐phenylpent‐2‐ene and 1‐perfluoroalkyl epoxy ethers: 1,1,1‐trifluoro‐2‐ethoxy‐2,3‐epoxy‐5‐phenylpentane

reactant: 32.3 g (70 mmol) of 3‐phenylpropyltriphenylphosphonium bromide (1)

product: (Z)‐1,1,1‐trifluoro‐2‐ethoxy‐5‐phenyl‐2‐pentene (3)

product: 1,1,1‐trifluoro‐2‐ethoxy‐2,3‐epoxy‐5‐phenylpentane (4)
Selective Protection of 1,3‐Diols at the More Hindered Hydroxy Group: 3‐(Methoxymethoxy)‐1‐Butanol
Authors: Bailey William F. , Carson Matthew W. , Zarcone Lyn M. J.
Published: November 2003

Selective Protection of 1,3‐diols at the more hindered hydroxy group: 3‐(methoxymethoxy)‐1‐butanol

intermediate: 1‐acetoxy‐3‐(methoxymethoxy)butane

product: 3‐(Methoxymethoxy)‐1‐butanol
6,7‐Dihydrocyclopenta‐1,3‐Dioxin‐5(4
H
)‐One
Authors: Chen Kwunmin , Brook Christopher S. , Smith Amos B.
Published: November 2003

(R,R)‐N,N′‐bis(3,5‐di‐tert‐butylsalicylidene)‐1,2‐cyclohexanediamino manganese(III) chloride, a highly enantioselective epoxidation catalyst

product: 6,7‐Dihydrocyclopenta‐1,3‐Dioxin‐5(4H)‐One
3‐Cyclopentene‐1‐Carboxylic Acid
Authors: Deprés Jean‐Pierre , Greene Andrew E.
Published: November 2003

3‐Cyclopentene‐1‐carboxylic Acid

intermediate: 3‐cyclopentene‐1,1‐dicarboxylic acid

product: 3‐cyclopentene‐1‐carboxylic acid
Synthesis of 8,8‐Dicyanoheptafulvene from Cycloheptatrienylium Tetrafluoroborate and Bromomalononitrile
Authors: Takeshita Hitoshi , Mori Akira , Kubo Kanji
Published: November 2003

Synthesis of 8,8‐dicyanoheptafulvene from cycloheptatrienylium tetrafluoroborate and bromomalononitrile

reactant: Bromomalononitrile (14.49 g, 0.1 mol)

product: 8,8‐dicyanoheptafulvene
1S‐(−)‐1,3‐Dithiane 1‐Oxide
Authors: Page Philip C. Bulman , Heer Jag P. , Bethell Donald , Collington Eric W. , Andrews David M.
Published: November 2003

1S‐(−)‐1,3‐dithiane 1‐oxide

intermediate: 2‐(2,2‐dimethylpropanoyl)‐1,3‐dithiane

intermediate: anti‐ and syn‐1S‐(2,2‐dimethylpropanoyl)‐1,3‐dithiane 1‐oxide

product: 1S‐(−)‐1,3‐dithiane 1‐oxide

reactant: (+)‐[(8,8‐dimethoxycamphoryl)sulfonyl]oxaziridine
1‐Chloro‐(2S,3S)‐Dihydroxycyclohexa‐4,6‐Diene
Authors: Hudlicky Tomas , Stabile Michele R. , Gibson David T. , Whited Gregory M.
Published: November 2003

1‐chloro‐(2S,3S)‐dihydroxycyclohexa‐4,6‐diene

product: 1‐chloro‐(2S,3S)‐dihydroxycyclohexa‐4,6‐diene
Methyl (S)‐2‐Phthalimido‐4‐Oxobutanoate
Authors: Meffre Patrick , Durand Philippe , Le Goffic François
Published: November 2003

Methyl (S)‐2‐phthalimido‐4‐oxobutanoate

intermediate: Methyl (S)‐2‐phthalimido‐4‐methylthiobutanoate

product: Methyl (S)‐2‐phthalimido‐4‐oxobutanoate
Dimethyl Squarate and its Conversion to 3‐Ethenyl‐4‐Methoxycyclobutene‐1,2‐Dione and 2‐Butyl‐6‐Ethenyl‐5‐Methoxy‐1,4‐Benzoquinone
Authors: Liu Hui , Tomooka Craig S. , Xu Simon L. , Yerxa Benjamin R. , Sullivan Robert W. , Xiong Yifeng , Moore Harold W.
Published: November 2003

Dimethyl squarate and its conversion to 3‐ethenyl‐4‐methoxycyclobutene‐1,2‐dione and 2‐butyl‐6‐ethenyl‐5‐methoxy‐1,4‐benzoquinone

product: Dimethyl squarate. (1)

product: 3‐Ethenyl‐4‐methoxycyclobutene‐1,2‐dione (2)

product: 2‐Butyl‐6‐ethenyl‐5‐methoxy‐1,4‐benzoquinone (3)

byproduct: methyl formate
Regioselective Monoalkylation of Ketones via their Manganese Enolates: 2‐Benzyl‐6‐Methylcyclohexanone from 2‐Methylcyclohexanone
Authors: Cahiez Gérard , Chau François , Blanchot Bernard
Published: November 2003

Regioselective monoalkylation of ketones via their manganese enolates: 2‐benzyl‐6‐methylcyclohexanone from 2‐methylcyclohexanone

product: 2‐benzyl‐6‐methylcyclohexanone

byproduct: 2‐benzyl‐2‐methylcyclohexanone
Isomerization of β‐Alkynyl Allylic Alcohols to Furans Catalyzed by Silver Nitrate on Silica Gel: 2‐Pentyl‐3‐Methyl‐5‐Heptylfuran
Authors: Marshall James A. , Sehon Clark A.
Published: November 2003

Isomerization of β‐alkynyl allylic alcohols to furans catalyzed by silver nitrate on silica gel: 2‐pentyl‐3‐methyl‐5‐heptylfuran

intermediate: 2‐bromo‐1‐octen‐3‐ol

intermediate: 7‐methylene‐8‐hexadecyn‐6‐ol

product: 2‐pentyl‐3‐methyl‐5‐heptylfuran
Transformation of Pseudoephedrine Amides into Highly Enantiomerically Enriched Aldehydes, Alcohols, and Ketones
Authors: Myers Andrew G. , Yang Bryant H. , Chen Hou
Published: November 2003

Transformation of pseudoephedrine amides into highly enantiomerically enriched aldehydes, alcohols, and ketones

product: (R)‐α‐methylbenzenepropanal

product: (R)‐β‐methylbenzenepropanol

product: (R)‐2‐methyl‐1‐phenyl‐3‐heptanone

product: (R)‐α‐methylbenzenepropanoic acid

byproduct: (R)‐3‐butyl‐2‐methyl‐1‐phenylheptan‐3‐ol
Synthesis of 1,1‐Dimethylethyl (S)‐4‐Formyl‐2,2‐Dimethyl‐3‐Oxazolidinecarboxylate by Oxidation of the Alcohol
Authors: Dondoni Alessandro , Perrone Daniela
Published: November 2003

Synthesis of 1,1‐dimethylethyl (S)‐4‐formyl‐2,2‐dimethyl‐3‐oxazolidinecarboxylate by oxidation of the alcohol

intermediate:N‐[(1,1‐Dimethylethoxy)carbonyl]‐L‐serine methyl ester(2).

intermediate: methyl serinate hydrochloride

intermediate:3‐(1,1‐Dimethylethyl) 4‐methyl‐(S)‐2,2‐dimethyloxazolidine‐3,4‐dicarboxylate(3).

intermediate:N‐[(1,1‐Dimethylethoxy)carbonyl]‐N,O‐isopropylidene‐L‐serinol(4).

product:1,1‐Dimethylethyl (S)‐4‐formyl‐2,2‐dimethyl‐3‐oxazolidinecarboxylate(5).
Diastereoselective Synthesis of Protected Vicinal Amino Alcohols: (S)‐2‐[(4S)‐N‐tert‐Butoxycarbonyl‐2,2‐Dimethyl‐1,3‐Oxazolidinyl]‐2‐tert‐Butyldimethylsiloxyethanal from a Serine‐Derived Aldehyde
Authors: Dondoni Alessandro , Perrone Daniela
Published: November 2003

Diastereoselective synthesis of protected vicinal amino alcohols: (S)‐2‐[(4S)‐N‐tert‐butoxycarbonyl‐2,2‐dimethyl‐1,3‐oxazolidinyl]‐2‐tert‐Butyldimethylsiloxyethanal from a serine‐derived aldehyde

intermediate: (S)‐2‐{[(4S)‐N‐tert‐Butoxycarbonyl‐2,2‐dimethyl‐1,3‐oxazolidin‐4‐yl]hydroxymethyl}‐1,3‐thiazole (2)

intermediate: (S)‐2‐{[(4S)‐N‐tert‐Butoxycarbonyl‐2,2‐dimethyl‐1,3‐oxazolidin‐4‐yl]‐tert‐butyldimethylsiloxy}‐1,3‐thiazole (3)

product: (S)‐2‐[(4S)‐N‐tert‐Butoxycarbonyl‐2,2‐dimethyl‐1,3‐oxazolidin‐4‐yl]‐2‐tert‐butyldimethylsiloxyethanal (4)

reactant: N‐Boc‐L‐serinal acetonide
The Synthesis of 2‐Alkyl‐4‐Pyrones from Meldrum's Acid
Authors: Crimmins Michael T. , Washburn David G. , Zawacki Frank J.
Published: November 2003

The synthesis of 2‐alkyl‐4‐pyrones from Meldrum's acid

intermediate: 5‐(1‐Hydroxyethylidene)‐2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione

product: 2‐methyl‐4H‐pyran‐4‐one
The
D
ess‐
M
artin Periodinane: 1,1,1‐Triacetoxy‐1,1‐Dihydro‐1,2‐Benziodoxol‐3(1H)‐One
Authors: Boeckman Robert K. , Shao Pengcheng , Mullins Joseph J.
Published: November 2003

The Dess‐Martin periodinane: 1,1,1‐triacetoxy‐1,1‐dihydro‐1,2‐benziodoxol‐3(1H)‐one

intermediate: 1‐Hydroxy‐1,2‐benziodoxol‐3(1H)‐one 1‐oxide (1)

product: 1,1,1‐Triacetoxy‐1,1‐dihydro‐1,2‐benziodoxol‐3(1H)‐one (2)
Synthesis of 2′‐Deoxyribonucleosides: β‐3′,5′‐Di‐O‐Benzoylthymidine
Authors: Prudhomme Daniel R. , Park Minnie , Wang Zhiwei , Buck Jason R. , Rizzo Carmelo J.
Published: November 2003

Synthesis of 2′‐deoxyribonucleosides: β‐3′,5′‐di‐O‐benzoylthymidine

intermediate: 1,3,5‐O‐tribenzoyl‐2‐O‐[(3‐trifluoromethyl)benzoyl]‐α‐D‐ribofuranose

intermediate: 2,4‐bis(trimethylsilyloxy)‐5‐methylpyrimidine

intermediate: 3′,5′‐di‐O‐benzoyl‐2′‐O‐[(3‐trifluoromethyl)benzoyl]‐5‐methyluridine

reactant: 9‐ethyl‐3,6‐dimethylcarbazole (200 mg, 0.9 mmol

product: 3′,5′‐di‐O‐benzoylthymidine

byproduct: 5′‐O‐benzoyl‐3′‐deoxythymidine
Bis(Pinacolato)Diboron
Authors: Ishiyama Tatsuo , Murata Miki , Ahiko Taka‐aki , Miyaura Norio
Published: November 2003

Bis(pinacolato)diboron

reactant: 218 g (4.84 mol) of dimethylamine

intermediate: tris(dimethylamino)borane

intermediate: bromobis(dimethylamino)borane

intermediate: tetrakis(dimethylamino)diboron

product: Bis(pinacolato)diboron
β‐Mercaptopropionitrile (2‐Cyanoethanethiol)
Authors: Gerber R. Eric , Hasbun Carlos , Dubenko Larisa G. , Fong King Mei , Bierer Donald E.
Published: November 2003

β‐Mercaptopropionitrile (2‐cyanoethanethiol)

intermediate:
2‐Cyanoethylthiouronium hydrochloride

product:
2‐Cyanoethanethiol

product:
3,3′‐Dithiobispropionitrile
Methyl 2,3‐O‐(6,6′‐Octahydro‐6,6′‐Bi‐2H‐Pyran‐2,2′‐Diyl)‐α‐
D
‐Galactopyranoside
Authors: Ley Steven V. , Osborn Helen M.I.
Published: November 2003

Methyl 2,3‐O‐(6,6′‐octahydro‐6,6′‐bi‐2H‐pyran‐2,2′‐diyl)‐α‐
D
‐galactopyranoside

intermediate: 6,6′‐bi(3,4‐dihydro‐2H‐pyran)

product: methyl 2,3‐O‐(6,6′‐octahydro‐6,6′‐bi‐2H‐pyran‐2,2′‐diyl)‐α‐D‐galactopyranoside
6
A
‐O‐p‐Toluenesulfonyl‐β‐Cyclodextrin
Authors: Brady Bernadette , Lynam Nuala , O'Sullivan Thomas , Ahern Cormac , Darcy Raphael
Published: November 2003

6
A
‐O‐p‐toluenesulfonyl‐β‐cyclodextrin

product: 6
A
‐O‐p‐toluenesulfonyl‐β‐cyclodextrin

product: Cyclodextrin monotosylate
Photochemical Synthesis of Bicyclo[1.1.1]Pentane‐1,3‐Dicarboxylic Acid
Authors: Levin Michael D. , Kaszynski Piotr , Michl Josef
Published: November 2003

Photochemical synthesis of bicyclo[1.1.1]pentane‐1,3‐dicarboxylic acid

intermediate: 1,3‐diacetylbicyclo[1.1.1]pentane

product: Bicyclo[1.1.1]pentane‐1,3‐dicarboxylic acid
Cyclopropene: A New Simple Synthesis and itsDiels‐Alder Reaction With Cyclopentadiene
Authors: Binger Paul , Wedemann Petra , Brinker Udo H.
Published: November 2003

Cyclopropene: A new simple synthesis and its Diels‐Alder reaction with cyclopentadiene

intermediate: Cyclopropene

product: endo‐tricyclo[3.2.1.02,4]oct‐6‐ene
2‐Thiophenealdehyde
Authors: Wiberg Kenneth B.
Published: November 2003

2‐Thiophenealdehyde

product: 2‐Thiophenealdehyde
Aromatic Aldehydes. Mesitaldehyde
Authors: Rieche A. , Gross H. , Höft E.
Published: November 2003

Aromatic aldehydes. mesitaldehyde

product: mesitaldehyde
The ultrastructure of the capillaries in the gingiva of alloxan‐induced diabetic rats
Authors: Gül Nursel , Özsoy Nesrin
Published: November 2003

The diabetic effects of alloxan (type I diabetes mellitus) were investigated in 40 Wistar albino rats (18 controls and 22 diabetics). Alloxan in sterile physiological saline was injected into animals intravenously. After the induction of diabetes with alloxan, the ultrastructure of the capillaries in the gingiva was examined by transmission electron microscopy. The thickness of the basement membranes was observed closely adherent to the endothelial cells of the capillary alloxan‐diabetic rats. It was greatly thickened owing to the increase in its amorphous, granular and filamentous material with occasional scattered collagen fibres. In some sections, the capillary lumens of the diabetics were closed by epithelial cells. Loss of cytoplasmic material and hyalinization were seen in some smooth muscle cells. In addition, the mitochondrial cristae of smooth muscle cell and epithelial cells disappeared. There was endothelial integrity throughout the smooth muscle cells. Copyright © 2003 John Wiley & Sons, Ltd.