DIASTEREOFACE DIFFERENTIATION IN ADDITION OF LITHIUM ENOLATES TO CHIRAL ALPHA,BETA-EPOXYALDEHYDES

被引：32

作者：

ESCUDIER, JM ^{[1
]}

BALTAS, M ^{[1
]}

GORRICHON, L ^{[1
]}

机构：

[1] UNIV TOULOUSE 3,CNRS,SYNTHESE & PHYSICOCHIM ORGAN LAB,118 ROUTE NARBONNE,F-31062 TOULOUSE,FRANCE

来源：

TETRAHEDRON | 1993年 / 49卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)82375-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldolisation reaction of lithium ester enolates with chiral alpha,beta-epoxyaldehydes 2a-2f has been investigated. The reaction proceeds with diastereofacial preference in favour of the anti isomer (anti:syn approximately 4:1) and can be greatly enhanced in the case of cis alpha,beta-epoxyaldehydes 2a-2c by a synergic effect of temperature and enolate excess (anti:syn 13:1). The Felkin-Ahn model can explain the results obtained on asymmetric induction.

引用

页码：5253 / 5266

页数：14

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