bluuebunny/crossref_metadata_2025_split huggingface dataset:
Reductive Cleavage of Vinyl Phosphorodiamidates: 17β‐
tert
‐Butoxy‐Gα‐androst‐2‐ene
Authors: Ireland Robert E. , O'Neil Thomas H. , Tolman Glen L. 
Published: November 2003

Abstract

Reductive cleavage of vinyl phosphorodiamidates: 17β‐
tert
‐butoxy‐Gα‐androst‐2‐ene

intermediate: vinyl phosphorodiamidate

intermediate: 1.61 g (4.6 mmol) of 17β‐tert‐butoxy‐5α‐androstan‐3‐one

reactant: N,N,N′,N′‐Tetramethyldiamidophosphorochloridate, 5.83 mL (0.038 mol)

product: 17β‐tert‐butoxy‐5α‐androst‐2‐ene
Palladium‐Catalyzed Synthesis of 1,4‐Dienes by Allylation of Alkenylalanes:α‐Farnesene
Authors: Negishi Ei‐ichi , Matsushita Hajime 
Published: November 2003

AbstractPalladium‐catalyzed synthesis of 1,4‐dienes by allylation of alkenylalanes:α‐farneseneproduct: α‐farneseneproduct: 6‐Z isomer of α‐farnesene
Reductive Arylation of Electron‐Deficient Olefins: 4‐(4‐Chlorophenyl)butan‐2‐one
Authors: Citterio Attilio 
Published: November 2003

Abstract

Reductive arylation of electron‐deficient olefins: 4‐(4‐chlorophenyl)butan‐2‐one

product: 4‐(4‐chlorophenyl)butan‐2‐one

product: semicarbazone
Preparation of Low‐Halide Methyllithium
Authors: Lusch Michael J. , Phillips William V. , Sieloff Ronald F. , Nomura Glenn S. , House Herbert O. 
Published: November 2003

Abstract

Preparation of Low‐Halide Methyllithium

reactant: methyl chloride

product: methyllithium

unknown: 1.0 mL of freshly distilled 1,2‐dibromoethane
Synthesis and
D
iels–
A
lder Reactions of 3‐Acetyl‐2(3
H
)‐oxazolone: 6‐Amino‐3,4‐dimethyl‐
cis
‐3‐cyclohexen‐1‐ol
Authors: Scholz Karl‐Heinz , Heine Hans‐Georg , Hartmann Willy 
Published: November 2003

Abstract

Synthesis and Diels–Alder reactions of 3‐acetyl‐2(3
H
)‐oxazolone: 6‐amino‐3,4‐dimethyl‐
cis
‐3‐cyclohexen‐1‐ol

intermediate: 326 g (3.75 mol) of 2‐oxazolidinone

intermediate: 258 g (2.0 mol) of 3‐acetyl‐2‐oxazolidinone

intermediate: 4‐Acetyl‐7,8‐dimethyl‐2‐oxa‐4‐azabicyclo[4.3.0]non‐7‐en‐3‐one.

product: 63.5 g (0.5 mol) of 3‐acetyl‐2(3H)‐oxazolone

product: 6‐Amino‐3,4‐dimethyl‐cis‐3‐cyclohexen‐1‐ol.
Thiation with 2,4‐Bis(4‐Methoxyphenyl)‐1,3,2,4‐ Dithiadiphosphetane 2,4‐Disulfide:N‐Methylthiopyrrolidone
Authors: Thomsen I. , Clausen K. , Scheibye S. , Lawesson S.‐O. 
Published: November 2003

AbstractThiation with 2,4‐bis(4‐methoxyphenyl)‐1,3,2,4‐ dithiadiphosphetane 2,4‐disulfide:N‐methylthiopyrrolidonereactant: 111.0 g (0.25 mol) of phosphorus sulfide, P4S10intermediate: 2,4‐bis(4‐methoxyphenyl)‐1,3,2,4‐dithiadiphosphetane 2,4‐disulfideproduct: N‐methylthiopyrrolidone
Acyloin Condensation by Thiazolium Ion Catalysis: Butyroin
Authors: Stetter H. , Kuhlmann H. 
Published: November 2003

Abstract

Acyloin condensation by thiazolium ion catalysis: butyroin

catalyst: 13.4 g (0.05 mol) of 3‐benzyl‐5‐(2‐hydroxyethyl)‐4‐methyl‐1,3‐thiazolium chloride

product: butyroin

product: furoin
Synthesis of α,β‐Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile
Authors: DiBiase Stephen A. , Beadle James R. , Gokel George W. 
Published: November 2003

AbstractSynthesis of α,β‐unsaturated nitriles from acetonitrile: cyclohexylideneacetonitrile and cinnamonitrileproduct: cinnamonitrileintermediate: cyclohexylideneacetonitrile
in situ
Cyanosilylation of Carbonyl Compounds:
O
‐Trimethylsilyl‐4‐Methoxymandelonitrile
Authors: Rasmussen J. K. , Heilmann S. M. 
Published: November 2003

Abstract

in situ cyanosilylation of carbonyl compounds:
O
‐trimethylsilyl‐4‐methoxymandelonitrile

product: colorless liquid

unknown: R
1
= C
6
H
5
, R
2
= H

unknown: R
1
= 4‐CH
3
C
6
H
4
, R
2
= H

unknown: R
1
= 2‐ClC
6
H
4
, R
2
= H

unknown: R
1
= 4‐ClC
6
H
4
, R
2
= H

unknown: R
1
= C
6
H
5
, R
2
= CH
3

unknown: R
1
, R
2
= (CH
2
)5

unknown: R
1
=
c
‐C
6
H
11
, R
2
= H
Asymmetric Hydrogenation of Ketopantoyl Lactone:D‐(−)‐Pantoyl Lactone
Authors: Ojima I. , Kogure T. , Yoda Y. 
Published: November 2003

AbstractAsymmetric hydrogenation of ketopantoyl lactone:D‐(−)‐pantoyl lactonereactant: 25.6 g (0.2 mol) of ketopantoyl lactoneproduct:D‐(−)‐pantoyl lactone
Optically Active Epoxides from Vicinal Diols via Vicinal Acetoxy Bromides: (
S
)‐( − )‐ and (
R
)‐( + )‐Methyloxirane
Authors: Ellis Martin K. , Golding Bernard T. 
Published: November 2003

Abstract

Optically active epoxides from vicinal diols via vicinal acetoxy bromides: (
S
)‐( − )‐ and (
R
)‐( + )‐methyloxirane

intermediate: (S)‐( + )‐propane‐1,2‐diol

intermediate: (S)‐( − )‐2‐acetoxy‐1‐bromopropane

product: (S)‐( − )‐methyloxirane

intermediate: (R)‐( + )‐2‐Acetoxy‐1‐bromopropane

product: (R)‐( + )‐Methyloxirane
Cyclopropanone Ethyl Hemiacetal from Ethyl 3‐Chloropropanoate
Authors: Salaün J. , Marguerite J. 
Published: November 2003

Abstract

Cyclopropanone ethyl hemiacetal from ethyl 3‐chloropropanoate

intermediate: 1‐ethoxy‐1‐(trimethylsilyloxy) cyclopropane

product: Cyclopropanone ethyl hemiacetal
Hexafluoroacetone
Authors: Puy Michael Van Der , Anello Louis G. 
Published: November 2003

Abstract

Hexafluoroacetone

intermediate: 60 g (0.165 mol) of 2,2,4,4‐tetrakis(trifluoromethyl)‐1,3‐dithietane

product: hexafluoroacetone (HFA)
Peptide Synthesis using 1‐(4‐Chlorophenyl)‐3‐(4′‐Methyl‐1′‐Piperazinyl)‐2‐Propyn‐1‐one as Reagent: Benzyloxycarbonyl‐
L
‐Alanyl‐
L
‐Cysteine Methyl Ester and Benzyloxycarbonyl‐
L
‐Aspartyl‐(
tert
‐Butyl Ester)‐
L
‐Phenylalanyl‐
L
‐Valine Methyl Ester
Authors: Fahrni H. P. , Lienhard U. , Neuenschwander M. 
Published: November 2003

Abstract

Peptide synthesis using 1‐(4‐chlorophenyl)‐3‐(4′‐methyl‐1′‐piperazinyl)‐2‐propyn‐1‐one as reagent: benzyloxycarbonyl‐
L
‐alanyl‐
L
‐cysteine methyl ester and benzyloxycarbonyl‐
L
‐aspartyl‐(
tert
‐butyl ester)‐
L
‐phenylalanyl‐
L
‐valine methyl ester

product: benzyloxycarbonyl‐L‐alanyl‐L‐cysteine methyl ester

product: benzyloxycarbonyl‐L‐aspartyl‐(tert‐butyl ester)‐L‐phenylalanyl‐L‐valine methyl ester

product: Cbz‐L‐Ala‐Gly‐OMe

product: Cbz‐L‐Ala‐L‐Val‐OMe

product: Cbz‐L‐Ala‐L‐Phe‐OMe

product: Cbz‐Gly‐L‐Phe‐Gly‐OEt

product: Cbz‐L‐Asp(O‐t‐Bu)‐L‐Phe‐L‐Val‐OMe

product: Cbz‐L‐Ile‐L‐Ile‐OBzl

product: Cbz‐L‐Ala‐L‐Ser‐OMe

product: Cbz‐L‐Ala‐L‐Tyr‐OMe

product: Cbz‐L‐Ala‐L‐Cys‐OMe

product: Cbz‐L‐Ala‐L‐Met‐OMe

product: Cbz‐L‐Ser‐Gly‐OEt
Hexahydro‐2‐(1
H
)‐Azocinone
Authors: Olah George A. , Fung Alexander P. 
Published: November 2003

Abstract

Hexahydro‐2‐(1
H
)‐azocinone

reactant: cycloheptanone (5.61 g, 0.05 mol)

product: hexahydro‐2(1H)‐azocinone
Indoles from 2‐Methylnitrobenzenes by Condensation with Formamide Acetals Followed by Reduction: 4‐Benzyloxyindole
Authors: Batcho Andrew D. , Leimgruber Willy 
Published: November 2003

Abstract

Indoles from 2‐Methylnitrobenzenes by Condensation with Formamide Acetals Followed by Reduction: 4‐Benzyloxyindole

intermediate: 6‐benzyloxy‐2‐nitrotoluene

intermediate: (E)‐6‐benzyloxy‐2‐nitro‐β‐pyrrolidinostyrene and (E)‐6‐benzyloxy‐β‐dimethylamino‐2‐nitrostyrene

product: 4‐benzyloxyindole

intermediate: pyrrolidine enamine, mp 108–110° (MeOH), and N,N‐dimethylenamine
Addition of an Ethylcopper Complex to 1‐Octyne: (
E
)‐5‐Ethyl‐1,4‐Undecadiene
Authors: Iyer Ramnath S. , Helquist Paul 
Published: November 2003

Abstract

Addition of an ethylcopper complex to 1‐octyne: (
E
)‐5‐ethyl‐1,4‐undecadiene

product: (
E
)‐5‐ethyl‐1,4‐undecadiene
α‐Amino Acetals: 2,2‐Diethoxy‐2‐(4‐Pyridyl)Ethylamine
Authors: LaMattina John L. , Suleske R. T. 
Published: November 2003

Abstract

α‐Amino acetals: 2,2‐diethoxy‐2‐(4‐pyridyl)ethylamine

reactant: Hydroxylamine hydrochloride (25.0 g, 0.36 mol)

reactant: 4‐acetylpyridine (36.3 g, 0.30 mol)

intermediate:
E
‐ and
Z
‐isomers of 4‐acetylpyridine oxime

intermediate:
E
‐4‐acetylpyridine oxime

product: 2,2‐Diethoxy‐2‐(4‐pyridyl)ethylamine.

intermediate:
E
)‐4‐acetylpyridine tosylate (55.1 g, 0.19 mol
Condensation of Dimethyl 1,3‐Acetonedicarboxylate with 1,2‐Dicarbonyl Compounds:
cis
‐bicyclo[3.3.0]octane‐3,7‐diones
Authors: Bertz Steven H. , Cook James M. , Gawish Ali , Weiss Ulrich 
Published: November 2003

Abstract

Condensation of Dimethyl 1,3‐Acetonedicarboxylate with 1,2‐Dicarbonyl Compounds:
cis
‐Bicyclo[3.3.0]octane‐3,7‐diones

intermediate: Tetramethyl 3,7‐dihydroxybicyclo[3.3.0]octa‐2,6‐diene‐2,4,6,8‐tetracarboxylate

product: cis‐Bicyclo[3.3.0]octane‐3,7‐dione

intermediate: Tetramethyl 3,7‐dihydroxy‐1,5‐dimethylbicyclo[3.3.0]octa‐2,6‐diene‐2,4,6,8‐tetracarboxylate

product: cis‐1,5‐Dimethylbicyclo[3.3.0]octane‐3,7‐dione

intermediate: C16H16O10Na2·H2O
Conversion of Epoxides to β‐Hydroxy Isocyanides:
trans
‐2‐Isocyanocyclohexanol
Authors: Gassman Paul G. , Guggenheim Thomas L. 
Published: November 2003

Abstract

Conversion of epoxides to β‐hydroxy isocyanides:
trans
‐2‐isocyanocyclohexanol

intermediate: [(trans‐2‐isocyanocyclohexyl)oxy]trimethylsilane

product: trans‐2‐isocyanocyclohexanol
The
S
tork–
D
anheiser Kinetic Alkylation Procedure: 3‐Ethoxy‐6‐methyl‐2‐cyclohexen‐1‐one
Authors: Kende Andrew S. , Fludzinski Pawel 
Published: November 2003

Abstract

The Stork–Danheiser kinetic alkylation procedure: 3‐Ethoxy‐6‐methyl‐2‐cyclohexen‐1‐one

product: 3‐ethoxy‐6‐methyl‐2‐cyclohexen‐1‐one
Hydroxylation of Enolates with Oxodiperoxymolybdenum(Pyridine)(Hexamethylphosphoric Triamide), MoO
5
·Py·HMPA(MoOPH): 3‐Hydroxy‐1,7,7‐Trimethylbicyclo[2.2.1]Heptan‐2‐one
Authors: Vedejs Edwin , Larsen S. 
Published: November 2003

Abstract

Hydroxylation of enolates with oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide), MoO
5
·Py·HMPA(MoOPH): 3‐hydroxy‐1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐one

intermediate: Oxodiperoxymolybdenum(aqua)(hexamethylphosphoric triamide), MoO5·H2O·HMPA

intermediate: Oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) MoO5·Py·HMPAMoOPH

product: 1,7,7‐trimethyl‐3‐hydroxybicyclo[2.2.1]‐heptan‐2‐one
α‐Hydroxylation of a Ketone Using
o
‐Iodosylbenzoic Acid: α‐Hydroxyacetophenone via the α‐Hydroxy Dimethylacetal
Authors: Moriarty Robert M. , Hou Kwang‐Chung , Prakash Indra , Arora S. K. 
Published: November 2003

Abstract

α‐Hydroxylation of a ketone using
o
‐iodosylbenzoic acid: α‐hydroxyacetophenone via the α‐hydroxy dimethylacetal

reactant: Anhydrous methanol (80 mL)

product: α‐Hydroxyacetophenone.

intermediate: 6.0 g (0.33 mol) of α‐hydroxy dimethylacetal
Stereocontrolled Iodolactonization of Acyclic Olefinic Acids: The
trans
and
cis
Isomers of 4,5‐Dihydro‐5‐Iodomethyl‐4‐Phenyl‐2(3
H
)‐Furanone
Authors: Gonzalez F. Bermejo , Bartlett Paul A. 
Published: November 2003

Abstract

Stereocontrolled iodolactonization of acyclic olefinic acids: The
trans
and
cis
isomers of 4,5‐dihydro‐5‐iodomethyl‐4‐phenyl‐2(3
H
)‐furanone

intermediate: 3‐phenyl‐4‐pentenoic acid

product: trans iodolactone

product:
cis
‐iodolactone

product: methyl (3
RS
,4
RS
)‐4,5‐epoxy‐3‐phenylpentanoate
Stereospecific Reduction of Propargyl Alcohols: (
E
)‐3‐Trimethylsilyl‐2‐Propen‐1‐ol
Authors: Jones Todd K. , Denmark Scott E. 
Published: November 2003

Abstract

Stereospecific reduction of propargyl alcohols: (
E
)‐3‐trimethylsilyl‐2‐propen‐1‐ol

intermediate: 3‐trimethylsilyl‐2‐propyn‐1‐ol

product: (
E
)‐3‐trimethylsilyl‐2‐propen‐1‐ol
Tris(Dimethylamino)Sulfonium Difluorotrimethylsilicate
Authors: Middleton William J. 
Published: November 2003

AbstractTris(dimethylamino)sulfonium difluorotrimethylsilicateproduct: tris(dimethylamino)sulfonium difluorotrimethylsilicatereactant:N,N‐Dimethylaminotrimethylsilane is available from Petrarch Systems, Inc.byproduct: hexamethyl‐disiloxane
The Stetter Reaction: 2,5‐Undecanedione and 3‐Methyl‐2‐Pentyl‐2‐Cyclopenten‐1‐one (Dihydrojasmone)
Authors: Stetter H. , Kuhlmann H. , Haese W. 
Published: November 2003

AbstractThe Stetter reaction: 2,5‐undecanedione and 3‐methyl‐2‐pentyl‐2‐cyclopenten‐1‐one (dihydrojasmone)product: 3‐Methyl‐2‐pentyl‐2‐cyclopenten‐1‐one (Dihydrojasmone).product: 2,5‐Undecanedione (92.1 g, 0.5 mol)
1,2,3,4,5‐Pentamethylcyclopentadiene
Authors: Threlkel Richard S. , Bercaw John E. , Seidler Paul F. , Stryker Jeffrey M. , Bergman Robert G. 
Published: November 2003

Abstract

1,2,3,4,5‐Pentamethylcyclopentadiene

product: 1,2,3,4,5‐Pentamethylcyclopentadiene
Alkoxycarbonylation of Propargyl Chloride: Methyl 4‐Chloro‐2‐butynoate
Authors: Olomucki M. , Gall J. Y. Le 
Published: November 2003

Abstract

Alkoxycarbonylation of propargyl chloride: methyl 4‐chloro‐2‐butynoate

product: methyl 4‐chloro‐2‐butynoate

product: 4‐Chloro‐2‐butynoic (chlorotetrolic) acid

product: ethyl 4‐chloro‐2‐butynoate

product: tert‐butyl 4‐chloro‐2‐butynoate
Dialkoxyacetylenes: di‐
tert
‐butoxyethyne, A Valuable Synthetic Intermediate
Authors: Bou Anna , Pericàs Miquel A. , Riera Antoni , Serratosa Fèlix 
Published: November 2003

Abstract

Dialkoxyacetylenes: di‐
tert
‐butoxyethyne, a valuable synthetic intermediate

intermediate:
trans
‐2,3‐dichloro‐1,4‐dioxane

intermediate:
trans
‐2‐
tert
‐butoxy‐3‐hydroxy‐1,4‐dioxane

intermediate:
trans
‐2,3‐di‐
tert
‐butoxy‐1,4‐dioxane

intermediate:
cis
‐ and
trans
‐2,3‐di‐
tert
‐butoxy‐1,4‐dioxane

intermediate: 1,2‐di‐
tert
‐butoxy‐1,2‐dichloroethane

intermediate: (
E
)‐1,2‐di‐
tert
‐butoxy‐1‐chloroethene

product: di‐
tert
‐butoxyethyne

byproduct: 0.1–0.5 g of
cis
‐2,3,7,10‐tetraoxabicyclo[4.4.0]decane

byproduct: (
Z
)‐1,2‐di‐
tert
‐butoxy‐1‐chloroethane

byproduct: 1,2,3‐tri‐
tert
‐butoxy‐3‐cyano‐1‐propene

byproduct: 1,2,3‐tri‐
tert
‐butoxy‐1‐cyano‐1‐propene
Ambient‐Temperature
U
llman Reaction: 4,5,4′,5′‐Tetramethoxy‐1,1′‐Biphenyl‐2,2′‐Dicarboxaldehyde
Authors: Ziegler F. E. , Fowler K. W. , Rodgers W. B. , Wester R. T. 
Published: November 2003

Abstract

Ambient‐temperature Ullman reaction: 4,5,4′,5′‐tetramethoxy‐1,1′‐biphenyl‐2,2′‐dicarboxaldehyde

intermediate: 6‐Bromo‐3,4‐dimethoxybenzaldehyde cyclohexylimine

reactant: cuprous iodidetriethyl phosphite complex

intermediate: 6‐iodoveratraldehyde cyclohexylimine

product: 4,5,4′,5′‐Tetramethoxy‐1,1′‐biphenyl‐2,2′‐carboxaldehyde (4)
Synthesis of a Key β‐Lactam Intermediate by a [2 + 2] Cycloaddition Route: 4‐Acetoxyazetidin‐2‐One
Authors: Mickel Stuart J. , Hsiao Shi‐Nung , Miller Marvin J. 
Published: November 2003

Abstract

Synthesis of a key β‐lactam intermediate by a [2 + 2] cycloaddition route: 4‐acetoxyazetidin‐2‐one

product: 4‐acetoxyazetidin‐2‐one
Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11‐Tetrathiacyclotetradecane
Authors: Buter J. , Kellogg Richard M. 
Published: November 2003

Abstract

Synthesis of macrocyclic sulfides using cesium thiolates: 1,4,8,11‐tetrathiacyclotetradecane

intermediate: 3,7‐dithianonane‐1,9‐diol

intermediate: 3,7‐dithianonane‐1,9‐dithiol

product: 1,4,8,11‐tetrathiacyclotetradecane
(−)‐8‐phenylmenthol
Authors: Ort Oswald 
Published: November 2003

Abstract

(−)‐8‐phenylmenthol

intermediate: (2RS,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexanone (2)

reactant: Grignard reagent

reactant: 40.0 g (0.26 mol) of (R)‐(+)‐pulegone

byproduct: biphenyl

product: (1RS,2SR,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexanol (3/4)

intermediate: (1R,2S,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexyl chloroacetate 5

product: (1R,2S,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexanol (3)
Copper‐Catalyzed Conjugate Addition of a Zinc Homoenolate: Ethyl 3‐[3‐(trimethylsilyloxy)cyclohex‐2‐enyl]propionate
Authors: Nakamura Eiichi , Kuwajima Isao 
Published: November 2003

Abstract

Copper‐catalyzed conjugate addition of a zinc homoenolate: ethyl 3‐[3‐(trimethylsilyloxy)cyclohex‐2‐enyl]propionate

product: Ethyl 3‐[3‐(Trimethylsilyloxy)cyclohex‐2‐enyl]propionate

product: 1‐Trimethylsilyloxy‐1‐ethoxycyclopropane
Palladium‐Catalyzed Synthesis of Conjugated Dienes: (5Z,7E)‐5,7‐Hexadecadiene
Authors: Negishi Ei‐Ichi , Takahashi Tamotsu , Baba Shigeru 
Published: November 2003

AbstractPalladium‐catalyzed synthesis of conjugated dienes: (5Z,7E)‐5,7‐hexadecadieneintermediate: (E)‐1‐decenyldiisobutylalaneproduct: (5Z,7E)‐5,7‐hexadecadiene
Vinyl Radical Cyclization via Addition of Tin Radicals to Triple Bonds: 3‐Methylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic Acid, Dimethyl Ester
Authors: Mook Robert , Sher Philip Michael 
Published: November 2003

Abstract

Vinyl radical cyclization via addition of tin radicals to triple bonds: 3‐Methylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic acid, dimethyl ester

intermediate: (3‐Methyl‐2‐butenyl)propanedioic acid, dimethyl ester (1)

intermediate: (3‐Methyl‐2‐butenyl)(2‐propynyl)propanedioic acid, dimethyl ester (2)

intermediate: (
Z
)‐3‐Tributylstannylmethylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic acid, dimethyl ester (3)

product: 3‐Methylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic acid, dimethyl ester (4)
Vinylation of Enolates with a Vinyl Cation Equivalent:
trans
‐3‐Methyl‐2‐Vinylcyclohexanone
Authors: Chang Tony C. T. , Rosenblum Myron , Simms Nancy 
Published: November 2003

Abstract

Vinylation of enolates with a vinyl cation equivalent:
trans
‐3‐methyl‐2‐vinylcyclohexanone

intermediate: Dicarbonyl(cyclopentadienyl)(ethyl vinyl ether)iron tetrafluoroborate (1).

intermediate: Dicarbonyl(cyclopentadientyl)(trans‐3‐methyl‐2‐vinylcyclohexanone)iron tetrafluoroborate (3).

product: trans‐3‐Methyl‐2‐vinylcyclohexanone (4).
Ketones from Carboxylic Acids and
G
rignard Reagents: Methyl 6‐Oxodecanoate
Authors: Fujisawa Tamotsu , Sato Toshio 
Published: November 2003

Abstract

Ketones from carboxylic acids and Grignard reagents: methyl 6‐oxodecanoate

reactant: 6.92 g (0.052 mol) of 1‐chloro‐N,N,2‐trimethylpropenylamine

reactant: 8.01 g (0.050 mol) of adipic acid monomethyl ester

product: methyl 6‐oxodecanoate
Trisammonium Geranyl Diphosphate
Authors: Woodside Andrew B. , Huang Zheng , Poulter C. Dale 
Published: November 2003

Abstract

Trisammonium geranyl diphosphate

reactant: 1.54 g (10 mmol) of geraniol

intermediate: 0.83 g (4.8 mmol) of geranyl chloride

product: trisammonium geranyl diphosphate
(
R
)‐(+)‐ and (
S
)‐(−)‐2,2′‐Bis(Diphenylphosphino)‐1,1′‐Binaphthyl (BINAP)
Authors: Takaya Hidemasa , Akutagawa Susumu , Noyori Ryoji 
Published: November 2003

Abstract

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

intermediate: 2,2′‐Dibromo‐1,1′‐binaphthyl

intermediate: (±)‐2,2′‐Bis(diphenylphosphinyl)‐1,1′‐binaphthyl [(±)‐BINAPO]

intermediate: (
R
)‐(+)‐BINAPO

intermediate: 1 : 1 complex of (
S
)‐BINAPO and (−)‐DBT

intermediate: (
S
)‐BINAPO

intermediate: ((
R
)‐BINAPO and (−)‐DBT)

intermediate: (
R
)‐BINAPO‐(+)‐DBT‐complex

product: (
S
)‐BINAP
(
R
)‐(−)‐
N,N
‐Diethyl‐(
E
)‐Citronellalenamine and (
R
)‐(+)‐Citronellal via Isomerization of
N,N
‐Diethylgeranylamine or
N,N
‐Diethylnerylamine
Authors: Tani Kazuhide , Yamagata Tsuneaki , Otsuka Sei , Kumobayashi Hidenori , Akutagawa Susumu 
Published: November 2003

Abstract

(
R
)‐(−)‐
N,N
‐diethyl‐(
E
)‐citronellalenamine and (
R
)‐(+)‐citronellal via isomerization of
N,N
‐diethylgeranylamine or
N,N
‐diethylnerylamine

catalyst: [(+)‐2,2′‐Bis(diphenylphosphino)‐1,1′‐binaphthyl]‐(η
4
‐1,5‐cyclooctadiene) rhodium(I) perchlorate. [
Rh
{(+)‐BINAP} (1,5‐C
8
H
12
)] ClO
4

catalyst: [(−)‐2,2′‐Bis(diphenylphosphino)‐1,1′‐binaphthyl] (η
4
‐1,5‐cyclooctadiene) rhodium(I) perchlorate: [
Rh
{(−)‐BINAP}(1,5‐C
8
H
12
)] ClO
4

reactant: 83.8 g (0.40 mol) of
N,N
‐diethylgeranylamine

product: (
R
)‐(−)‐
N,N
‐diethyl‐(
E
)‐citronellalenamine

reactant: 83.8 g (0.40 mol) of
N,N
‐diethylnerylamine

product: (+)‐citronellal

catalyst: [Rh{(−)‐BINAP} (1,5‐C
8
H
12
)]ClO
4
THF

product: (
S
)‐(−)‐
N
‐cyclohexylcitronellalimine

product: (
R
)‐(−)‐
N,N
‐dimethyl‐3‐phenyl‐1(
E
)‐butenylamine
(−)‐Salsolidine
Authors: Meyers Albert I. , Boes Michael , Dickman Daniel A. 
Published: November 2003

Abstract

(−)‐Salsolidine

intermediate: 6,7‐Dimethoxy‐1,2,3,4‐tetrahydro‐2‐[(1‐tert‐butoxy‐3‐methyl)‐2‐butyliminomethyl]isoquinoline

reactant: 10.0 g (51.7 mmol) of 6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline 1

byproduct: valinol tert‐butyl ether

product: (S)‐6,7‐dimethoxy‐1‐methyl‐1,2,3,4‐tetrahydroisoquinoline (salsolidine)
α‐Diphenylmethylsilylation of Ester Enolates: 2‐Methyl‐2‐Undecene from Ethyl Decanoate
Authors: Larson Gerald L. , Lopez‐Cepero Ingrid Montes de , Mieles Luis Rodriguez 
Published: November 2003

Abstract

α‐Diphenylmethylsilylation of ester enolates: 2‐methyl‐2‐undecene from ethyl decanoate

reactant: 10.3 mL (11.6 g; 50 mmol) of diphenylmethylchlorosilane in 40 mL of tetrahydrofuran

intermediate: ethyl 2‐(diphenylmethylsilyl)decanoate

product: 2‐Methyl‐2‐undecene
N
‐Benzyl‐
N
‐methoxymethyl‐
N
‐(trimethylsilyl)methylamine as an Azomethine Ylide Equivalent: 2,6‐dioxo‐1‐phenyl‐4‐benzyl‐1,4‐diazabicyclo[3.3.0]octane
Authors: Padwa Albert , Dent William 
Published: November 2003

Abstract

N
‐benzyl‐
N
‐methoxymethyl‐
N
‐(trimethylsilyl)methylamine as an azomethine ylide equivalent: 2,6‐dioxo‐1‐phenyl‐4‐benzyl‐1,4‐diazabicyclo[3.3.0]octane

intermediate: N‐benzyl‐N‐(trimethylsilyl)methylamine

intermediate: N‐benzyl‐N‐methoxymethyl‐N‐(trimethylsilyl)methylamine

product: 2,6‐dioxo‐1‐phenyl‐4‐benzyl‐1,4‐diazabicyclo[3.3.0]octane
N
‐Acetyl‐
N
‐Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene Using Hydrazine and Rhodium on Carbon
Authors: Oxley P. W. , Adger B. M. , Sasse M. J. , Forth M. A. 
Published: November 2003

Abstract

N
‐acetyl‐
N
‐phenylhydroxylamine via catalytic transfer hydrogenation of nitrobenzene using hydrazine and rhodium on carbon

solvent: 100 mL of petroleum ether

product: N‐acetyl‐N‐phenylhydroxylamine
Preparation and Use of Lithium Acetylide: 1‐Methyl‐2‐ethynyl‐
endo
‐3,3‐dimethyl‐2‐norbornanol
Authors: Midland M. Mark , McLoughlin Jim I. , Werley Ralph T. 
Published: November 2003

Abstract

Preparation and use of lithium acetylide: 1‐methyl‐2‐ethynyl‐
endo
‐3,3‐dimethyl‐2‐norbornanol

product: 1‐Methyl‐2‐ethynyl‐
endo
‐3,3‐dimethyl‐2‐norbornanol
DiastereoselectiveAldol Condensation Using a Chiral Oxazolidinone Auxiliary: (2
S
*,3
S
*)‐3‐Hydroxy‐3‐phenyl‐2‐methylpropanoic Acid
Authors: Gage James R. , Evans David A. 
Published: November 2003

Abstract

Diastereoselective aldol condensation using a chiral oxazolidinone auxiliary: (2
S
*,3
S
*)‐3‐hydroxy‐3‐phenyl‐2‐methylpropanoic acid

intermediate: (
S
)‐3‐(1‐Oxopropyl)‐4‐(phenylmethyl)‐2‐oxazolidinone

intermediate: aldol adduct

intermediate: oxazolidinone auxiliary

product: (2S*,3S*)‐3‐hydroxy‐3‐hydroxy‐3‐phenyl‐2‐methylpropanoic acid
Palladium‐catalyzed reaction of 1‐alkenylboronates with vinylic halides: (1
Z
,3
E
)‐1‐phenyl‐1,3‐octadiene
Authors: Miyaura Norio , Suzuki Akira 
Published: November 2003

Abstract

Palladium‐catalyzed reaction of 1‐alkenylboronates with vinylic halides: (1
Z
,3
E
)‐1‐phenyl‐1,3‐octadiene

intermediate: (E)‐1‐Hexenyl‐1,3,2‐benzodioxaborole.

reactant: 6.7 mL (60 mmol) of catecholborane

product: (1Z,3E)‐1‐phenyl‐1,3‐octadiene
Palladium‐Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta‐3,5‐diene
Authors: Cacchi Sandro , Morera Enrico , Ortar Giorgio 
Published: November 2003

Abstract

Palladium‐catalyzed reduction of vinyl trifluoromethanesulfonates to alkenes: cholesta‐3,5‐diene

intermediate: cholesta‐3,5‐dien‐3‐yl trifluoromethanesulfonate

product: cholesta‐3,5‐diene
Stereoselective 1,4‐Functionalizations of Conjugated Dienes:
cis
‐ and
trans
‐1‐Acetoxy‐4‐(Dicarbomethoxymethyl)‐2‐Cyclohexene
Authors: Bäckvall Jan‐E. , Vågberg Jan O. 
Published: November 2003

Abstract

Stereoselective 1,4‐functionalizations of conjugated dienes:
cis
‐ and
trans
‐1‐acetoxy‐4‐(dicarbomethoxymethyl)‐2‐cyclohexene

intermediate:
cis
‐1‐acetoxy‐4‐chloro‐2‐cyclohexene

intermediate:
cis
‐1‐acetoxy‐4‐(dicarbomethoxymethyl)‐2‐cyclohexene

product:
trans
‐1‐acetoxy‐4‐(dicarbomethoxymethyl)‐2‐cyclohexene
1,3,4,6‐Tetra‐
O
‐Acetyl‐2‐Deoxy‐α‐
D
‐Glucopyranose
Authors: Giese Bernd , Gröninger Kay S. 
Published: November 2003

Abstract

1,3,4,6‐Tetra‐
O
‐acetyl‐2‐deoxy‐α‐
D
‐Glucopyranose

product: 1,3,4,6‐tetra‐O‐acetyl‐2‐deoxy‐α‐D‐glucopyranose
Mixed Higher‐Order Cyanocuprate‐Induced Epoxide Openings: 1‐Benzyloxy‐4‐Penten‐2‐ol
Authors: Lipshutz Bruce H. , Moretti Robert , Crow Robert 
Published: November 2003

Abstract

Mixed higher‐order cyanocuprate‐induced epoxide openings: 1‐benzyloxy‐4‐penten‐2‐ol

reactant: (±)‐benzyl 2,3‐epoxypropyl ether (7.34 g, 44.7 mmol, 83%)

product: (R)‐1‐Benzyloxy‐4‐penten‐2‐ol