ASYMMETRIC INDUCTION IN THE BAYLIS-HILLMAN REACTION

被引：62

作者：

GILBERT, A ^{[1
]}

HERITAGE, TW ^{[1
]}

ISAACS, NS ^{[1
]}

机构：

[1] UNIV READING,DEPT CHEM,POB 224,READING RG6 2AD,BERKS,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(00)86138-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric induction in the product of the Baylis-Hillman reaction between an aldehyde and an acrylic compound in the presence of a tertiary amine base, may be controlled by chirality in the aldehyde, acrylic ester, base or solvent; R-CHO + CH2 = CH-COOR' (B:, solvent) --> CH2 = C(C*HROH)-COOR' Examples of each are described but the best stereochemical result, 100% ee, is obtained from the high pressure reaction of benzaldehyde with (-)-menthyl acrylate.

引用

页码：969 / 972

页数：4

共 5 条

[1] Baylis A. B., 1972, Patent No. [2155113A1, 2155113]
[2] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES
DREWES, SE
ROOS, GHP
[J]. TETRAHEDRON, 1988, 44 (15) : 4653 - 4670
[3] FUNCTIONALIZATION OF THE ALPHA-POSITION OF ACRYLATE SYSTEMS BY THE ADDITION OF CARBONYL-COMPOUNDS - HIGHLY PRESSURE-DEPENDENT REACTIONS
HILL, JS
ISAACS, NS
[J]. TETRAHEDRON LETTERS, 1986, 27 (41) : 5007 - 5010
[4] DABCO-CATALYZED COUPLING OF ALDEHYDES WITH ACTIVATED DOUBLE-BONDS .1. PREPARATION OF 2-(1-HYDROXYALKYL)ACRYLIC ESTERS - SIMPLE 3-STEP SYNTHESIS OF MIKANECIC ACID
HOFFMANN, HMR
RABE, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10): : 795 - 796
[5] SYNTHESIS AND REACTIONS OF ALPHA-METHYLENE-BETA-KETO SULFONES
WEICHERT, A
HOFFMANN, HMR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) : 4098 - 4112

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