ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES

被引：153

作者：

CAIN, CM ^{[1
]}

COUSINS, RPC ^{[1
]}

COUMBARIDES, G ^{[1
]}

SIMPKINS, NS ^{[1
]}

机构：

[1] UNIV LONDON QUEEN MARY COLL,DEPT CHEM,LONDON E1 4NS,ENGLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)85435-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of chiral secondary amines have been prepared and used as precursors to the corresponding chiral lithium amide bases. Treatment of either cis-2,6-dimethylcyclohexanone or 4-tert-butylcyclohexanone with a chiral lithium amide, followed by electrophilic quench, gives chiral products in up to 88% enantiomeric excess. The results with 4-tert-butylcyclohexanone are in disagreement with an earlier literature report, giving products of lower enantiomeric excess but higher optical rotation. © 1990.

引用

页码：523 / 544

页数：22

共 28 条

[1] BIGGS J, 1970, J CHEM SOC CHEM COMM, P1506
[2] PREPARATION, STEREOCHEMISTRY, AND NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF METHYL 1,3-DIMETHYL-2-OXOCYCLOHEXANEACETATES AND RELATED DERIVATIVES
BRANCA, SJ
SMITH, AB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (06) : 1026 - 1030
[3] CONCISE ASYMMETRIC-SYNTHESIS OF (5S, 6S)- AEGINETOLIDE AND (5S)- DIHYDROACTINIDIOLIDE
CAIN, CM
SIMPKINS, NS
[J]. TETRAHEDRON LETTERS, 1987, 28 (32) : 3723 - 3724
[4] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE
COREY, EJ
GROSS, AW
[J]. TETRAHEDRON LETTERS, 1984, 25 (05) : 495 - 498
[5] COUSINS RPC, UNPUB TETRAHEDRON LE
[6] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[7] DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL SECONDARY-AMINES WITH 2 CHIRAL CENTERS DIRECTLY ATTACHED TO THE NITROGEN ATOM
ELEVELD, MB
HOGEVEEN, H
SCHUDDE, EP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) : 3635 - 3642
[8] INDUCIBILITY OF AN ENONE REDUCTASE SYSTEM IN THE FUNGUS BEAUVERIA-SULFURESCENS - APPLICATION IN ENANTIOSELECTIVE ORGANIC-SYNTHESIS
FAUVE, A
RENARD, MF
VESCHAMBRE, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) : 4893 - 4897
[9] FRASER RR, 1984, J ORG CHEM, V49, P3442, DOI 10.1021/jo00192a059
[10] (R,R)-1,3-DIBENZYLISOINDOLINE - A NEW C2-SYMMETRIC SECONDARY AMINE, BY STEREOSELECTIVE AND REGIOSELECTIVE ALPHA,ALPHA'-DIALKYLATION OF ISOINDOLINE, AND AN IMPROVED PROCEDURE FOR THE PREPARATION OF ISOINDOLINE
GAWLEY, RE
CHEMBURKAR, SR
SMITH, AL
ANKLEKAR, TV
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22) : 5381 - 5383

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