bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthesis of 2‐Substituted Naphthalenediol Derivatives using Chromium Carbene Complexes: 1‐Acetoxy‐2‐Butyl‐4‐Methoxynaphthalene
Authors: Timko Joseph M. , Yamashita Ayako 
Published: November 2003

Abstract

Synthesis of 2‐substituted naphthalenediol derivatives using chromium carbene complexes: 1‐acetoxy‐2‐butyl‐4‐methoxynaphthalene

unknown: 20.0 g (64.0 mmol) of pentacarbonyl[phenyl(methoxy)chromium]carbene

product: 1‐acetoxy‐2‐butyl‐4‐methoxynaphthalene
A Hydroxymethyl Anion Equivalent: Tributyl[(Methoxymethoxy)Methyl]Stannane
Authors: Danheiser Rick L. , Romines Karen R. , Koyama Hiroo , Gee Stephen K. , Johnson Carl R. , Medich John R. 
Published: November 2003

Abstract

A hydroxymethyl anion equivalent: tributyl[(methoxymethoxy)methyl]stannane

intermediate: (tributylstannyl)methanol

reactant: Boron trifluoride etherate (13.0 mL, 0.106 mol)

product: tributyl[(methoxymethoxy)methyl]stannane
Preparation and use of (Methoxymethoxy)Methyllithium: 1‐(Hydroxymethyl)Cycloheptanol
Authors: Johnson Carl R. , Medich John R. , Danheiser Rick L. , Romines Karen R. , Koyama Hiroo , Gee Stephen K. 
Published: November 2003

Abstract

Preparation and use of (methoxymethoxy)methyllithium: 1‐(hydroxymethyl)cycloheptanol

intermediate: 1‐[(methoxymethoxy)methyl]cycloheptanol

product: 1‐[hydroxymethyl)cycloheptanol
Ethyl 1‐Naphthylacetate: Ester Homologation via Ynolate Anions
Authors: Reddy Rajarathnam E. , Kowalski Conrad J. 
Published: November 2003

Abstract

Ethyl 1‐naphthylacetate: ester homologation via ynolate anions

product: ethyl 1‐naphthylacetate
Inverse Electron‐Demand
D
iels‐
A
lderCycloaddition of a Ketene Dithioacetal. Copper Hydride‐Promoted Reduction of a Conjugated Enone. 9‐Dithiolanobicyclo[3.2.2]Non‐6‐En‐2‐One from Tropone
Authors: Dahnke Karl R. , Paquette Leo A. 
Published: November 2003

Abstract

Inverse electron‐demand Diels‐Alder cycloaddition of a ketene dithioacetal. Copper hydride‐promoted reduction of a conjugated enone. 9‐dithiolanobicyclo[3.2.2]non‐6‐en‐2‐one from tropone

intermediate: tropone

intermediate: 9‐dithiolanobicyclo[3.2.2]nona‐3,6‐dien‐2‐one

product: 9‐Dithiolanobicyclo[3.2.2]non‐6‐en‐2‐one
A Selective, Heterogeneous Oxidation Using A Mixture of Potassium Permanganate and Cupric Sulfate: (3as,7ar)‐Hexahydro‐(3S,6R)‐Dimethyl‐2(3H)‐Benzofuranone
Authors: Jefford Charles W. , Li Yun , Wang Ying 
Published: November 2003

Abstract

A selective, heterogeneous oxidation using a mixture of potassium permanganate and cupric sulfate: (3aS,7aR)‐hexahydro‐(3S,6R)‐dimethyl‐2(3H)‐benzofuranone

reactant: 31 g (0.20 mol) of isopulegol

intermediate: (−)‐(1R,3R,4S,8R)‐p‐menthane‐3,9‐diol

product: 3aS,7aR‐hexahydro‐3S,6R‐dimethyl‐2(3H)‐benzofuranone
9‐Bromo‐9‐Phenylfluorene
Authors: Jamison T. F. , Lubell W. D. , Dener J. M. , Krisché M. J. , Rapoport H. 
Published: November 2003

Abstract

9‐Bromo‐9‐phenylfluorene

product: 9‐bromo‐9‐phenylfluorene

intermediate: 9‐phenyl‐9‐fluorenol
(S)‐N‐(9‐Phenylfluoren‐9‐yl)Alanine and (S)‐Dimethyl N‐(9‐Phenylfluoren‐9‐yl)Aspartate
Authors: Jamison T. F. , Rapoport H. 
Published: November 2003

Abstract

(S)‐N‐(9‐phenylfluoren‐9‐yl)alanine and (S)‐dimethyl N‐(9‐phenylfluoren‐9‐yl)aspartate

product: (S)‐N‐(9‐Phenylfluoren‐9‐yl)alanine (2)

reactant: L‐alanine (1, 13.5 g, 150 mmol,)

product: (S)‐Dimethyl N‐(9‐phenylfluoren‐9‐yl)aspartate (4)

byproduct: 9‐methoxy‐9‐phenylfluorene (5.30 g, 19.5 mmol,)

byproduct: 9‐phenyl‐9‐fluorenol (2.00 g, 7.7 mmol,)

reactant: (S)‐Dimethyl aspartate hydrochloride
D‐(R)‐Glyceraldehyde Acetonide
Authors: Schmid Christopher R. , Bryant Jerry D. 
Published: November 2003

Abstract

D‐(R)‐glyceraldehyde acetonide

product: 2,3‐O‐isopropylidene‐D‐glyceraldehyde

intermediate: 1,2:5,6‐diisopropylidene‐D‐mannitol
(3S,4S)‐3‐Amino‐1‐(3,4‐Dimethoxybenzyl)‐4‐[(R)‐2,2‐Dimethyl‐1,3‐Dioxolan‐4‐yl]‐2‐Azetidinone
Authors: Hubschwerlen Christian , Specklin Jean‐Luc 
Published: November 2003

Abstract

(3S,4S)‐3‐amino‐1‐(3,4‐dimethoxybenzyl)‐4‐[(R)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]‐2‐azetidinone

intermediate: 100 g of phthalylglycyl chloride (90% based on phthalylglycine)

product: (3S,4S)‐3‐amino‐1‐(3,4‐dimethoxybenzyl)‐4‐[(R)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]‐2‐azetidinone

intermediate: N‐[(2R,3R)‐cis‐1‐(3,4‐Dimethoxybenzyl)‐2‐[(S)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]‐4‐oxo‐3‐azetidinyl]phthalimide
(1R,5R)‐(+)‐Verbenone of High Optical Purity
Authors: Sivik Mark R. , Stanton Kenetha J. , Paquette Leo A. 
Published: November 2003

Abstract

(1R,5R)‐(+)‐verbenone of high optical purity

reactant: (1R)‐(+)‐α‐Pinene (25.0 g, 0.183 mol

intermediate: mixture of acetates

product: verbenone
Chiral (Acyloxy)Borane Complex‐Catalyzed Asymmetric
D
iels‐
A
lder Reaction: (1R)‐1,3,4‐Trimethyl‐3‐Cyclohexene‐1‐Carboxaldehyde
Authors: Furuta Kyoji , Gao Qing‐Zhi , Yamamoto Hisashi 
Published: November 2003

Abstract

Chiral (acyloxy)borane complex‐catalyzed asymmetric Diels‐Alder reaction: (1R)‐1,3,4‐trimethyl‐3‐cyclohexene‐1‐carboxaldehyde

intermediate: (−)‐dibenzyl tartrate

intermediate: dibenzyl mono(2,6‐dimethoxybenzoyl)tartrate

intermediate: mono(2,6‐dimethoxybenozyl)tartaric acid

product: (1R)‐1,3,4‐trimethyl‐3‐cyclohexene‐1‐carboxaldehyde
Rearrangement of trans‐Stilbene Oxide to Diphenylacetaldehyde with Catalytic Methylaluminum bis(4‐Bromo‐2,6‐Di‐tert‐Butylphenoxide)
Authors: Ooi Takashi , Maruoka Keiji , Yamamoto Hisashi 
Published: November 2003

Abstract

Rearrangement of trans‐stilbene oxide to diphenylacetaldehyde with catalytic methylaluminum bis(4‐bromo‐2,6‐di‐tert‐butylphenoxide)

intermediate: 4‐bromo‐2,6‐di‐tert‐butylphenol

product: diphenylacetaldehyde

byproduct: Tischenko product
Synthesis of Functionalized Enynes by Palladium/Copper‐Catalyzed Coupling Reactions of Acetylenes with (Z)‐2,3‐Dibromopropenoic acid Ethyl Ester: (Z)‐2‐Bromo‐5‐(Trimethylsilyl)‐2‐Penten‐4‐ynoic Acid Ethyl Ester
Authors: Myers Andrew G. , Dragovich Peter S. 
Published: November 2003

Abstract

Synthesis of functionalized enynes by palladium/copper‐catalyzed coupling reactions of acetylenes with (Z)‐2,3‐dibromopropenoic acid ethyl ester: (Z)‐2‐bromo‐5‐(trimethylsilyl)‐2‐penten‐4‐ynoic acid ethyl ester

intermediate: (Z)‐2,3‐dibromo‐2‐propenoic acid ethyl ester

byproduct: bis(trimethylsilyl)butadiyne

product: (Z)‐2‐Bromo‐5‐(trimethylsilyl)‐2‐penten‐4‐ynoic acid ethyl ester

byproduct: (E)‐2‐[(trimethylsilyl)ethynyl]‐5‐(trimethylsilyl)‐2‐penten‐4‐ynoic acid ethyl ester
7‐Methoxyphthalide
Authors: Wang X. , de Silva S. O. , Reed J. N. , Billadeau R. , Griffen E. J. , Chan A. , Snieckus V. 
Published: November 2003

Abstract7‐Methoxyphthalideintermediate: N,N‐diethyl‐2‐methoxybenzamideintermediate: N,N‐Diethyl‐2‐formyl‐6‐methoxybenzamideproduct: 7‐methoxyphthalide
A Water‐Soluble Tin Hydride: Tris[3‐(2‐Methoxyethoxy)Propyl]Stannane
Authors: Light James , Breslow Ronald 
Published: November 2003

Abstract

A water‐soluble tin hydride: tris[3‐(2‐methoxyethoxy)propyl]stannane

intermediate: 3‐(2‐Methoxyethoxy)propene (1)

intermediate: 1‐Bromo‐3‐(2‐methoxyethoxy)propane (2)

intermediate: Tetra[3‐(2‐methoxyethoxy)propyl]stannane (3)

intermediate: Bromotris[3‐(2‐methoxyethoxy)propyl]stannane (4)

intermediate: Tris[3‐(2‐methoxyethoxy)propyl]stannane (5)
Reaction of Sulfoxides with Diethylaminosulfur Trifluoride: Fluoromethyl Phenyl Sulfone, A Reagent for the Synthesis of Fluoroalkenes
Authors: McCarthy James R. , Matthews Donald P. , Paolini John P. 
Published: November 2003

Abstract

Reaction of sulfoxides with diethylaminosulfur trifluoride: fluoromethyl phenyl sulfone, a reagent for the synthesis of fluoroalkenes

intermediate: fluoromethyl phenyl sulfide 1

product: fluoromethyl phenyl sulfone (2)
(3,3‐Difluoroallyl)Trimethylsilane
Authors: Gonzalez Javier , Foti Matthew J. , Elsheimer Seth 
Published: November 2003

Abstract

(3,3‐difluoroallyl)trimethylsilane

reactant: dibromodifluoromethane (83.9 g, 36.5 mL, 0.4 mol)

intermediate: (1,3‐dibromo‐3,3‐difluoropropyl)trimethylsilane (78.3 g, 0.25 mol)

intermediate: 3‐bromo‐3,3‐difluoropropyltrimethylsilane

product: (3,3‐difluoroallyl)trimethylsilane
Stereoselective Synthesis of 2,2‐Disubstituted 1‐Fluoro‐Alkenes: (E)‐[[Fluoro(2‐Phenylcyclohexylidene)‐Methyl]Sulfonyl]Benzene and (Z)‐[2‐(Fluoromethylene)‐Cyclohexyl]Benzene
Authors: McCarthy James R. , Matthews Donald P. , Paolini John P. 
Published: November 2003

Abstract

Stereoselective synthesis of 2,2‐disubstituted 1‐fluoro‐alkenes: (E)‐[[fluoro(2‐phenylcyclohexylidene)‐methyl]sulfonyl]benzene and (Z)‐[2‐(fluoromethylene)‐cyclohexyl]benzene

product: (E)‐[[Fluoro(2‐phenylcyclohexylidene)methyl]sulfonyl]benzene (1)

reactant: diethyl chlorophosphate (24.8 g, 0.14 mol)

intermediate: (E)‐Tributyl[fluoro(2‐phenylcyclohexylidene)methyl]stannane (2)

product: (Z)‐[2‐(Fluoromethylene)cyclohexyl]benzene (3)
3‐[(1S)‐1,2‐Dihydroxyethyl]‐1,5‐Dihydro‐3H‐2,4‐Benzodioxepine
Authors: Oi Ryu , Sharpless K. Barry 
Published: November 2003

Abstract

3‐[(1S)‐1,2‐dihydroxyethyl]‐1,5‐dihydro‐3H‐2,4‐benzodioxepine

intermediate: 1,2‐benzenedimethanol

intermediate: 3‐vinyl‐1,5‐dihydro‐3H‐2,4‐benzodioxepine

catalyst: dihydroquinidine 9‐O‐(9′‐phenanthryl) ether and, [0.75 g, (1.5 mmol, 1 mol%, 0.0057 M in the organic phase)]

product: 3‐[(1S)‐1,2‐dihydroxyethyl)]‐1,5‐dihydro‐3H‐2,4‐benzodioxepine
(1R,5S)‐(−)‐6,6‐Dimethyl‐3‐Oxabicyclo[3.1.0]Hexan‐2‐One. Highly Enantioselective Intramolecular Cyclopropanation Catalyzed by Dirhodium(II) Tetrakis[Methyl 2‐Pyrrolidone‐5(R)‐Carboxylate]
Authors: Doyle Michael P. , Winchester William R. , Protopopova Marina N. , Kazala Amy P. , Westrum Larry J. 
Published: November 2003

Abstract

(1R,5S)‐(−)‐6,6‐dimethyl‐3‐oxabicyclo[3.1.0]hexan‐2‐one. Highly enantioselective intramolecular cyclopropanation catalyzed by dirhodium(II) tetrakis[methyl 2‐pyrrolidone‐5(R)‐carboxylate]

intermediate: (−)‐Methyl 2‐pyrrolidone‐5(R)‐carboxylate

intermediate: (+)‐Dirhodium(II) tetrakis[methyl 2‐pyrrolidone‐5(R)‐carboxylate]

intermediate: 3‐Methyl‐2‐buten‐1‐yl acetoacetate

intermediate: 3‐Methyl‐2‐buten‐1‐yl diazoacetate

product: (1R,5S)‐(−)‐6,6‐Dimethyl‐3‐oxabicyclo[3.1.0]hexan‐2‐one

reactant: (R)‐(+)‐2‐Pyrrolidone‐5‐carboxylic acid [Fluka Chemika‐BioChemika, D‐pyroglutamic acid,

$[\alpha]^{22}_{\rm D}$

+9 ± 1° (H
2
O, c 5)]
EnantioselectiveHydrolysis of cis‐3,5‐Diacetoxycyclopentene: (1R,4S)‐(+)‐4‐Hydroxy‐2‐Cyclopentenyl Acetate
Authors: Deardorff Donald R. , Windham Colin Q. , Craney Chris L. 
Published: November 2003

Abstract

Enantioselective hydrolysis of cis‐3,5‐diacetoxycyclopentene: (1R,4S)‐(+)‐4‐hydroxy‐2‐cyclopentenyl acetate

reactant: 16.70 g (118 mmol) of (±)‐cis‐4‐acetoxy‐1‐hydroxycyclopent‐2‐ene [(±)‐1]

intermediate: cis‐3,5‐diacetoxycyclopentene (2)

product: (1R,4S)‐(+)‐4‐hydroxy‐2‐cyclopentenyl acetate [(+)‐1]
(4R)‐(+)‐tert‐Butyldimethylsiloxy‐2‐Cyclopenten‐1‐one
Authors: Paquette Leo A. , Earle Martyn J. , Smith Graham F. 
Published: November 2003

Abstract

(4R)‐(+)‐tert‐Butyldimethylsiloxy‐2‐Cyclopenten‐1‐one

reactant: 23 g (162 mmol) of (1R,4S)‐(+)‐4‐hydroxy‐2‐cyclopentenyl acetate

solvent: petroleum ether

intermediate: (4R)‐(+)‐acetoxy‐2‐cyclopenten‐1‐one

intermediate: 7.7 g (78 mmol) of (4R)‐(+)‐hydroxy‐2‐cyclopenten‐1‐one

product: (4R)‐(+)‐tert‐butyldimethylsiloxy‐2‐cyclopenten‐1‐one
Synthesis of β‐Lactones and Alkenes via Thiol Esters: (E)‐2,3‐Dimethyl‐3‐Dodecene
Authors: Danheiser Rick L. , Nowick James S. , Lee Janette H. , Miller Raymond F. , Huboux Alexandre H. 
Published: November 2003

Abstract

Synthesis of β‐lactones and alkenes via thiol esters: (E)‐2,3‐dimethyl‐3‐dodecene

reactant: 45.0 g (0.17 mol) of S‐phenyl decanoate

intermediate: β‐lactone

product: (E)‐2,3‐dimethyl‐3‐dodecene

solvent: petroleum ether (Mallinkrodt Inc., bp 35–60°C)
Regio‐ and StereoselectiveIntramolecularHydrosilylation of α‐Hydroxy Enol Ethers: 2,3‐syn‐2‐Methoxymethoxy‐1,3‐Nonanediol
Authors: Tamao Kohei , Nakagawa Yoshiki , Ito Yoshihiko 
Published: November 2003

Abstract

Regio‐ and stereoselective intramolecular hydrosilylation of α‐hydroxy enol ethers: 2,3‐syn‐2‐methoxymethoxy‐1,3‐nonanediol

intermediate: 2‐Bromoethyl methoxymethyl ether

intermediate: Methoxymethyl vinyl ether

intermediate: 2‐Methoxymethoxy‐1‐nonen‐3‐ol.

product: 2‐Methoxymethoxy‐1,3‐nonanediol
A General Procedure for
M
itsunobu Inversion of Sterically Hindered Alcohols: Inversion of Menthol. (1S,2S,5R)‐5‐Methyl‐2‐(1‐Methylethyl)Cyclohexyl 4‐Nitrobenzoate
Authors: Dodge Jeffrey A. , Nissen Jeffrey S. , Presnell Misti 
Published: November 2003

Abstract

A General procedure for Mitsunobu inversion of sterically hindered alcohols: inversion of menthol. (1S,2S,5R)‐5‐methyl‐2‐(1‐methylethyl)cyclohexyl 4‐nitrobenzoate

product: (1S,2S,5R)‐5‐Methyl‐2‐(1‐methylethyl)cyclohexyl 4‐nitrobenzoate
Detrifluoroacetylative Diazo Group Transfer: (E)‐1‐Diazo‐4‐Phenyl‐3‐Buten‐2‐One
Authors: Danheiser Rick L. , Miller Raymond F. , Brisbois Ronald G. 
Published: November 2003

Abstract

Detrifluoroacetylative diazo group transfer: (E)‐1‐diazo‐4‐phenyl‐3‐buten‐2‐one

product: (E)‐1‐diazo‐4‐phenyl‐3‐buten‐2‐one

product: α‐diazoacetophenone
Bis(Trifluoroethyl) (Carboethoxymethyl)Phosphonate
Authors: Patois Carl , Savignac Philippe , About‐Jaudet Elie , Collignon Noël 
Published: November 2003

Abstract

Bis(trifluoroethyl) (carboethoxymethyl)phosphonate

intermediate: bis(trifluoroethyl) methylphosphonate (1)

product: bis(trifluoroethyl) (carboethoxymethyl) phosphonate (2)
3‐Pyrroline
Authors: Meyers Albert I. , Warmus Joseph S. , Dilley Garrett J. 
Published: November 2003

Abstract

3‐Pyrroline

intermediate: 1‐[(Z)‐4‐Chloro‐2‐butenyl]‐1‐azonia‐3,5,7‐triazatricyclo[3.3.1.13,7]decane chloride (2)

intermediate: (Z)‐4‐Chloro‐2‐butenylammonium chloride (3)

product: 3‐pyrroline (4)
Diethyl (Dichloromethyl)Phosphonate. Preparation and use in the Synthesis of Alkynes: (4‐Methoxyphenyl)Ethyne
Authors: Marinetti Angela , Savignac Philippe 
Published: November 2003

Abstract

Diethyl (dichloromethyl)phosphonate. Preparation and use in the Synthesis of Alkynes: (4‐Methoxyphenyl)Ethyne

intermediate: diethyl (dichloromethyl)phosphonate, 1

product: (4‐methoxyphenyl)ethyne
Preparation of Polyquinanes by Double Addition of Vinyl Anions to Squarate Esters: 4,5,6,6a‐Tetrahydro‐3a‐Hydroxy‐2,3‐Diisopropoxy‐4,6a‐Dimethyl‐1(3aH)‐Pentalenone
Authors: Morwick Tina , Paquette Leo A. 
Published: November 2003

Abstract

Preparation of polyquinanes by double addition of vinyl anions to squarate esters: 4,5,6,6a‐tetrahydro‐3a‐hydroxy‐2,3‐diisopropoxy‐4,6a‐dimethyl‐1(3aH)‐pentalenone

product: 4,5,6,6a‐tetrahydro‐3a‐hydroxy‐2,3‐diisopropoxy‐4,6a‐dimethyl‐1(3aH)‐pentalenone

product: diquinane
Regio‐ and StereoselectiveCarboxylation of Allylic Barium Reagents: (E)‐4,8‐Dimethyl‐3,7‐Nonadienoic Acid
Authors: Yanagisawa Akira , Yasue Katsutaka , Yamamoto Hisashi 
Published: November 2003

Abstract

Regio‐ and stereoselective carboxylation of allylic barium reagents: (E)‐4,8‐dimethyl‐3,7‐nonadienoic acid

product: (E)‐4,8‐Dimethyl‐3,7‐nonadienoic acid

reactant: 2.8 g of biphenyl

product: (E)‐C
7
H
15
CHCHCH
2
CO
2
H

product: (Z)‐C
7
H
15
CHCHCH
2
CO
2
H

product: (CH
3
)
2
CCHCH
2
CO
2
H
Preparation of 3‐Bromopropiolic Esters:Methyl and tert‐Butyl 3‐Bromopropiolates
Authors: Leroy J. 
Published: November 2003

Abstract

Preparation of 3‐bromopropiolic esters: methyl and tert‐butyl 3‐bromopropiolates

product: methyl 3‐bromopropiolate

product: tert‐butyl 3‐bromopropiolate

product: Ethyl 3‐iodopropiolate
5,7‐Dimethoxy‐3‐Methylindazole from 3,5‐Dimethoxyacetophenone
Authors: Boudreault Nicolas , Leblanc Yves 
Published: November 2003

Abstract

5,7‐Dimethoxy‐3‐methylindazole from 3,5‐dimethoxyacetophenone

intermediate: 1‐(2‐Acetyl‐4,6‐dimethoxyphenyl)‐1,2‐hydrazinedicarboxylic acid bis(2,2,2‐trichloroethyl) ester

product: 5,7‐Dimethoxy‐3‐methylindazole
Regioselective Synthesis of 3‐Substituted Indoles: 3‐Ethylindole
Authors: Amat Mercedes , Hadida Sabine , Sathyanarayana Swargam , Bosch Joan 
Published: November 2003

Abstract

Regioselective synthesis of 3‐substituted indoles: 3‐ethylindole

intermediate: 3‐bromo‐1‐(tert‐butyldimethylsilyl)indole

intermediate: 1‐(tert‐butyldimethylsilyl)‐3‐ethylindole

product: 3‐ethylindole
3‐Morpholino‐2‐Phenylthioacrylic Acid Morpholide and 5‐(4‐Bromobenzoyl‐2‐(4‐Morpholino)‐3‐Phenylthiophene
Authors: Rolfs Andreas , Liebscher Jürgen 
Published: November 2003

Abstract

3‐Morpholino‐2‐phenylthioacrylic acid morpholide and 5‐(4‐bromobenzoyl‐2‐(4‐morpholino)‐3‐phenylthiophene

intermediate: 22.3 g (0.1 mol) of phenylthioacetic acid morpholide

product: 5‐(4‐Bromobenzoyl)‐2‐morpholino‐3‐phenylthiophene

product: 3.18 g (0.01 mol) of 3‐morpholino‐2‐phenylthioacrylic acid morpholide
(R,R)‐N,N′‐Bis(3,5‐di‐tert‐Butylsalicylidene)‐1,2‐Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst
Authors: Larrow Jay F. , Jacobsen Eric N. 
Published: November 2003

Abstract

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

intermediate: (R,R)‐1,2‐diammoniumcyclohexane mono‐(+)‐tartrate

reactant: 53.7 g (0.229 mol, 2.0 eq) of 3,5‐di‐tert‐butylsalicylaldehyde in 250 mL of ethanol

product: (R,R)‐N,N′‐Bis(3,5‐di‐tert‐butylsalicylidene)‐1,2‐cyclohexanediamino manganese(III) chloride.

intermediate: 50.0 g (0.09 mol, 1 eq) of (R,R)‐N,N′‐bis(3,5‐di‐tert‐butylsalicylidene)‐1,2‐cyclohexanediamine in 250 mL of toluene
Synthesis of Unsymmetrical Biaryls Using a Modified Suzuki Cross‐Coupling: 4‐Biphenylcarboxaldehyde
Authors: Huff Bret E. , Koenig Thomas M. , Mitchell David , Staszak Michael A. 
Published: November 2003

Abstract

Synthesis of unsymmetrical biaryls using a modified suzuki cross‐coupling: 4‐biphenylcarboxaldehyde

product: 4‐biphenylcarboxaldehyde
N‐Benzyl‐2,3‐Azetidinedione
Authors: Behrens Carsten , Paquette Leo A. 
Published: November 2003

Abstract

N‐benzyl‐2,3‐azetidinedione

intermediate: methyl 3‐hydroxy‐2‐methylenebutanoate

intermediate: Methyl 2‐(benzylamino)methyl‐3‐hydroxybutanoate

intermediate: N‐benzyl‐3‐(1‐hydroxyethyl)azetidin‐2‐one

intermediate: N‐Benzyl‐3‐(Z/E)‐ethylideneazetidin‐2‐one

product: N‐benzylazetidine‐2,3‐dione
Synthesis of 4‐(2‐Bromo‐2‐Propenyl)‐4‐Methyl‐γ‐Butyrolactone by the Reaction of Ethyl Levulinate with (2‐Bromoallyl)Diisopropoxyborane Prepared by Haloboration of Allene
Authors: Hara Shoji , Suzuki Akira 
Published: November 2003

Abstract

Synthesis of 4‐(2‐bromo‐2‐propenyl)‐4‐methyl‐γ‐butyrolactone by the reaction of ethyl levulinate with (2‐bromoallyl)diisopropoxyborane prepared by haloboration of allene

intermediate: (2‐bromoallyl)diisopropoxyborane

reactant: ethyl levulinate (9.96 g, 0.069 mol) in 30 mL of dry tetrahydrofuran

product: 4‐(2‐bromo‐2‐propenyl)‐4‐methyl‐γ‐butyrolactone
Preparation of Cyanoalkynes: 3‐Phenyl‐2‐Propynenitrile
Authors: Luo Fen‐Tair , Wang May‐Wen , Wang Ren‐Tzong 
Published: November 2003

Abstract

Preparation of cyanoalkynes: 3‐phenyl‐2‐propynenitrile

product: 3‐phenyl‐2‐propynenitrile

product: n‐C
5
CCCN

product: n‐C
6
CCCN
2‐Trimethylsilylethanesulfonyl Chloride (SES‐Cl)
Authors: Weinreb Steven M. , Chase Charles E. , Wipf Peter , Venkatraman Srikanth 
Published: November 2003

Abstract2‐Trimethylsilylethanesulfonyl chloride (SES‐Cl)intermediate: sodium β‐trimethylsilylethanesulfonateproduct: 2‐Trimethylsilylethylsulfonyl chloride (2)
(1′S,2′S)‐Methyl‐3O,4O‐(1′,2′‐Dimethoxycyclohexane‐1′,2′‐Diyl)‐α‐D‐Mannopyranoside
Authors: Ley Steven V. , Osborn Helen M. I. , Priepke Henning W. M. , Warriner Stuart L. 
Published: November 2003

Abstract

(1′S,2′S)‐methyl‐3O,4O‐(1′,2′‐dimethoxycyclohexane‐1′,2′‐diyl)‐α‐D‐mannopyranoside

intermediate: 1,1,2,2‐tetramethoxycyclohexane

product: (1′S,2′S)‐methyl‐3O,4O‐(1′,2′‐dimethoxycyclohexane‐1′,2′‐diyl)‐α‐D‐mannopyranoside
Use of 1,2,4,5‐Tetrabromobenzene as a 1,4‐Benzadiyne Equivalent: anti‐ and syn‐1,4,5,8‐Tetrahydroanthracene 1,4:5,8‐Diepoxides
Authors: Shahlai Khalil , Acquaah Samuel Osafo , Hart Harold 
Published: November 2003

Abstract

Use of 1,2,4,5‐Tetrabromobenzene as a 1,4‐Benzadiyne Equivalent: anti‐ and syn‐1,4,5,8‐Tetrahydroanthracene 1,4:5,8‐diepoxides

product: anti‐ and syn‐1,4,5,8‐Tetrahydroanthracene 1,4:5,8‐Diepoxides
(R)‐(+)‐ and (S)‐(−)‐2,2′‐Bis(Diphenylphosphino)‐1,1′‐Binaphthyl (BINAP)
Authors: Cai Dongwei , Payack Joseph F. , Bender Dean R. , Hughes David L. , Verhoeven Thomas R. , Reider Paul J. 
Published: November 2003

Abstract

(R)‐(+)‐ and (S)‐(−)‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP)

product: (R)‐(+)‐BINAP

intermediate: ditriflate of binaphthol (11.0 g, 20 mmol)
(2S,3S)‐(+)‐(3‐Phenylcyclopropyl)Methanol
Authors: Charette André B. , Lebel Hélène 
Published: November 2003

Abstract

(2S,3S)‐(+)‐(3‐phenylcyclopropyl)methanol

reactant: 24 mL (0.22 mol) of bromobutane

reactant: 10 mL (89.2 mmol) of trimethyl borate

intermediate: [(2‐)‐N,O,O′[2,2′‐Iminobis[ethanolato]]]‐2‐butylboron,

intermediate: 5.15 g (50.5 mmol) of butylboronic acid

intermediate: (4R‐trans)‐2‐Butyl‐N,N,N′,N′‐tetramethyl[1,3,2]dioxaborolane‐4,5‐dicarboxamide

reactant: 11.9 g (58.3 mmol) of (R,R)‐(+)‐N,N,N′,N′‐tetramethyltartaric acid diamide

product: (2S,3S)‐(+)‐(3‐phenylcyclopropyl)methanol
Synthesis of Chiral Non‐Racemic Diols from (S,S)‐1,2,3,4‐Diepoxybutane: (2S,3S)‐Dihydroxy‐1,4‐Diphenylbutane
Authors: Robbins Michael A. , Devine Paul N. , Oh Taeboem 
Published: November 2003

Abstract

Synthesis of chiral non‐racemic diols from (S,S)‐1,2,3,4‐diepoxybutane: (2S,3S)‐dihydroxy‐1,4‐diphenylbutane

intermediate: 2,3‐O‐isopropylidene‐L‐threitol 1,4‐bismethanesulfonate (40 g, 0.126 mol)

intermediate: L‐threitol 1,4‐bismethanesulfonate (25.0 g, 0.0898 moles)

product: (2S,3S)‐Dihydroxy‐1,4‐diphenylbutane

intermediate: (S,S)‐1,2,3,4‐Diepoxybutane (2.84 g, 0.033 mol, 11 mL of a 3 M solution in THF)
(tert‐Butyldimethylsilyl)Allene
Authors: Myers Andrew G. , Zheng Bin 
Published: November 2003

Abstract

(tert‐butyldimethylsilyl)allene

intermediate: 2‐propargyloxytetrahydropyran

intermediate: 3‐(tert‐butyldimethylsilyl)‐2‐propyn‐1‐ol

catalyst: 13.0 g (60.0 mmol) of o‐nitrobenzenesulfonyl hydrazide

product: (tert‐butyldimethylsilyl)allene
[3 + 4] Annulation Using a [β‐(Trimethylsilyl)Acryloyl]Silane and the Lithium Enolate of an α,β‐Unsaturated Methyl Ketone: (1R*,6S*,7S*)‐4‐(Tert‐Butyldimethylsiloxy)‐6‐(Trimethylsilyl)Bicyclo[5.4.0]Undec‐4‐En‐2‐One
Authors: Takeda Kei , Nakajima Akemi , Takeda Mika , Yoshii Eiichi 
Published: November 2003

Abstract

[3 + 4] Annulation using a [β‐(trimethylsilyl)acryloyl]silane and the lithium enolate of an α,β‐unsaturated methyl ketone: (1R,6S,7S)‐4‐(tert‐butyldimethylsiloxy)‐6‐(trimethylsilyl)bicyclo[5.4.0]undec‐4‐en‐2‐one

intermediate: 3‐(1‐ethoxyethoxy)‐1‐propyne

intermediate: 1‐(1‐ethoxyethoxy)‐1,2‐propadiene

intermediate: 1‐(tert‐butyldimethylsilyl)‐1‐(1‐ethoxyethoxy)‐1,2‐propadiene (2)

intermediate: (E)‐1‐(tert‐Butyldimethylsilyl)‐3‐trimethylsilyl‐2‐propen‐1‐one (3)

product: (1R,6S,7S)‐4‐(tert‐Butyldimethylsiloxy)‐6‐(trimethylsilyl)bicyclo[5.4.0]‐undec‐4‐en‐2‐one (4)
Synthesis and DiastereoselectiveAlkylation of Pseudoephedrine Amides
Authors: Myers Andrew G. , Yang Bryant H. 
Published: November 2003

Abstract

Synthesis and diastereoselective alkylation of pseudoephedrine amides

intermediate: (1S,2S)‐pseudoephedrinepropionamide

product: (1S,2S)‐pseudoephedrine‐(R)‐2‐methylhydrocinnamamide
(R)‐(+)‐2‐Hydroxy‐1,2,2‐Triphenylethyl Acetate
Authors: Macor John , Sampognaro Anthony J. , Verhoest Patrick R. , Mack Robert A. 
Published: November 2003

Abstract(R)‐(+)‐2‐hydroxy‐1,2,2‐triphenylethyl acetateproduct: (R)‐(+)‐2‐hydroxy‐1,2,2‐triphenylethyl acetatereactant: 1,1,2‐triphenyl‐1,2‐ethanediol
O
4
,O
5
‐Isopropylidene‐1,2:3,6‐Dianhydro‐
D
‐Glucitol from Isosorbide
Authors: Ejjiyar S. , Saluzzo C. , Amouroux R. 
Published: November 2003

Abstract

O
4
,O
5
‐isopropylidene‐1,2:3,6‐dianhydro‐
D
‐glucitol from isosorbide

reactant: O
4
,O
5
‐Isopropylidene‐3,6‐anhydro‐1‐deoxy‐1‐iodo‐
D
‐glucitol (1)

product: O
4
,O
5
‐Isopropylidene‐1,2:3,6‐dianhydro‐
D
‐glucitol (2)

solvent: petroleum ether