ENHANCED DIASTEREO AND ENANTIOSELECTIVITY IN THE FORMATION OF ACYLDITHIOLANE SULFOXIDES BY THE ASYMMETRIC OXIDATION OF THEIR ENOLSILYL ETHERS

Authors
BARROS MT LEITAO AJ MAYCOCK CD
Citation
Mt. Barros et al., ENHANCED DIASTEREO AND ENANTIOSELECTIVITY IN THE FORMATION OF ACYLDITHIOLANE SULFOXIDES BY THE ASYMMETRIC OXIDATION OF THEIR ENOLSILYL ETHERS, Tetrahedron letters, 38(28), 1997, pp. 5047-5050
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
28
Year of publication
1997
Pages
5047 - 5050
Database
ISI
SICI code
0040-4039(1997)38:28<5047:EDAEIT>2.0.ZU;2-H
Abstract
The sulphoxidation of the enol ethers of some acyldithiolanes using th e Sharpless epoxidation reagents followed by fluorolysis results in be tter overall stereoselectivity than direct oxidation of the acyldithio lane thus providing a highly stereoselective route to acyldithiolane s ulphoxides. Fluorolysis under acid conditions of non terminal enol eth ers results in complete racemisation of the product. (C) 1997 Publishe d by Elsevier Science Ltd.