DIRECT ASYMMETRIC ALPHA-HYDROXYLATION OF BETA-HYDROXYKETONES

Authors
LOPP M PAJU A KANGER T PEHK T
Citation
M. Lopp et al., DIRECT ASYMMETRIC ALPHA-HYDROXYLATION OF BETA-HYDROXYKETONES, Tetrahedron letters, 38(28), 1997, pp. 5051-5054
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
28
Year of publication
1997
Pages
5051 - 5054
Database
ISI
SICI code
0040-4039(1997)38:28<5051:DAAOB>2.0.ZU;2-3
Abstract
Direct oxidation of racemic beta-hydroxyketones 1a-c under Sharpless o xidation conditions resulted in the enantiomeric alpha,beta-dihydroxyk etones 2a in 97% ee, 2b in 86% ee and 29 in 95% ee respectively, in 37 -58% of isolated yield. The oxidation is assumed to proceed via an all ylic enolate intermediate. (C) 1997 Elsevier Science Ltd.