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

Authors
ESCUDIER JM BALTAS M GORRICHON L
Citation
Jm. Escudier et al., DIASTEREOFACE DIFFERENTIATION IN ADDITION OF LITHIUM ENOLATES TO CHIRAL ALPHA,BETA-EPOXYALDEHYDES, Tetrahedron, 49(24), 1993, pp. 5253-5266
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
24
Year of publication
1993
Pages
5253 - 5266
Database
ISI
SICI code
0040-4020(1993)49:24<5253:DDIAOL>2.0.ZU;2-Y
Abstract
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:sy n approximately 4:1) and can be greatly enhanced in the case of cis al pha,beta-epoxyaldehydes 2a-2c by a synergic effect of temperature and enolate excess (anti:syn 13:1). The Felkin-Ahn model can explain the r esults obtained on asymmetric induction.