Asymmetric synthesis of beta-hydroxyesters by aldol type condensation of enantiomerically pure t-butyl p-tolyl sulfinyl acetate: unexpected substituent effect on the absolute configuration of the product

Authors
Solladie, G Bauder, C Arce-Dubois, E Pasturel-Jacope, Y
Citation
G. Solladie et al., Asymmetric synthesis of beta-hydroxyesters by aldol type condensation of enantiomerically pure t-butyl p-tolyl sulfinyl acetate: unexpected substituent effect on the absolute configuration of the product, TETRAHEDR L, 42(15), 2001, pp. 2923-2925
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
15
Year of publication
2001
Pages
2923 - 2925
Database
ISI
SICI code
0040-4039(20010409)42:15<2923:ASOBBA>2.0.ZU;2-Z
Abstract
Aldol type condensation of enantiomerically pure t-butyl p-tolyl sulfinyl a cetate was shown to give the opposite configuration at the hydroxylic cente r in the case of an alpha,beta -unsaturated aldehyde, a result which is in sharp contrast with literature results. The absolute configurations of the aldol products were determined by X-ray crystallography. (C) 2001 Elsevier Science Ltd. All rights reserved.