STEREOSELECTIVE HYDROGENATION OF ALPHA-SULFINYL RADICAL GENERATED FROM ALKYL RADICAL-ADDITION TO ALPHA-(1-HYDROXYETHYL)VINYL SULFOXIDE

Authors
MASE N WAKE S WATANABE Y TORU T
Citation
N. Mase et al., STEREOSELECTIVE HYDROGENATION OF ALPHA-SULFINYL RADICAL GENERATED FROM ALKYL RADICAL-ADDITION TO ALPHA-(1-HYDROXYETHYL)VINYL SULFOXIDE, Tetrahedron letters, 39(31), 1998, pp. 5553-5556
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
31
Year of publication
1998
Pages
5553 - 5556
Database
ISI
SICI code
0040-4039(1998)39:31<5553:SHOARG>2.0.ZU;2-V
Abstract
The reaction of (2S,S-S)-alpha-(1-hydroxyethyl)vinyl sulfoxide with al kyl radicals and tributyltin hydride gave the addilion-hydrogenation p roducts with high diastereoselectivity, whereas (2R,S-S)-alpha-(-1-hyd roxyethyl)vinyl sulfoxide gave no products under similar conditions. A n important role of intramolecular hydrogen bonding for the diastereos electivity as well as the reactivity toward alkyl radicals is discusse d. (C) 1998 Elsevier Science Ltd. All rights reserved.