Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active alpha,beta-epoxyaldehydes

Authors
Nacro, K Baltas, M Gorrichon, L
Citation
K. Nacro et al., Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active alpha,beta-epoxyaldehydes, TETRAHEDRON, 55(49), 1999, pp. 14013-14030
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
49
Year of publication
1999
Pages
14013 - 14030
Database
ISI
SICI code
0040-4020(199912)55:49<14013:ATRTDI>2.0.ZU;2-Q
Abstract
Aldol condensations on alpha-,beta-epoxyaldehyde having a remote alkoxy gro up have been realized. A rationalization of the outcome of this condensatio n is discussed, relying on the dominant conformers revealed by molecular mo deling of anti and sny gamma,delta-epoxy beta-hydroxyesters and their NMR a nd IR spectrostroscopic properties. (C) 1999 Elsevier Science Ltd. All righ ts reserved.