ENHANCED DIASTEREOSELECTIVITY IN THE ADDITION OF ESTER ENOLATE TO OPTICALLY-ACTIVE ALPHA,BETA-EPOXYALDEHYDES OBTAINED FROM NEROL AND GERANIOL

Authors
NACRO K BALTAS M ESCUDIER JM GORRICHON L
Citation
K. Nacro et al., ENHANCED DIASTEREOSELECTIVITY IN THE ADDITION OF ESTER ENOLATE TO OPTICALLY-ACTIVE ALPHA,BETA-EPOXYALDEHYDES OBTAINED FROM NEROL AND GERANIOL, Tetrahedron, 52(27), 1996, pp. 9047-9056
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
27
Year of publication
1996
Pages
9047 - 9056
Database
ISI
SICI code
0040-4020(1996)52:27<9047:EDITAO>2.0.ZU;2-U
Abstract
Optically active alpha,beta-epoxyaldehydes obtained from nerol and ger aniol were allowed to react with lithium tert-butylacetate. The diaste reofacial preference of the aldolisation reaction was always anti (''S i''face attack of the carbonyl). The best diastereoselectivity ever ob served in these series (>99 : <1 anti : syn) was obtained for the alph a,beta-epoxyneral aldolisation. Copyright (C) 1996 Elsevier Science Lt d