Oxygen atom transfer from a chiral N-alkyl oxaziridine promoted by acid. The asymmetric oxidation of sulfides to sulfoxides.

Authors
Bohe, L Lusinchi, M Lusinchi, X
Citation
L. Bohe et al., Oxygen atom transfer from a chiral N-alkyl oxaziridine promoted by acid. The asymmetric oxidation of sulfides to sulfoxides., TETRAHEDRON, 55(1), 1999, pp. 155-166
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
1
Year of publication
1999
Pages
155 - 166
Database
ISI
SICI code
0040-4020(19990101)55:1<155:OATFAC>2.0.ZU;2-G
Abstract
Chiral N-alkyl oxaziridines may be used as reagents for the asymmetric oxid ation of sulfides in an acid-promoted reaction leading exclusively to the c orresponding sulfoxides A planar transition state geometry seems consistent with the observed stereochemistry which should result from the steric inte ractions in the transition state. The influence of the solvent and the acid strength on the oxygen transfer reaction are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.