SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXYCARBONYL COMPOUNDS BY (SALEN)MN(III)-CATALYZED OXIDATION OF SILYL ENOL ETHERS AND SILYL KETENE ACETALS

Authors
ADAM W FELL RT MOCKKNOBLAUCH C SAHAMOLLER CR
Citation
W. Adam et al., SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXYCARBONYL COMPOUNDS BY (SALEN)MN(III)-CATALYZED OXIDATION OF SILYL ENOL ETHERS AND SILYL KETENE ACETALS, Tetrahedron letters, 37(36), 1996, pp. 6531-6534
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
36
Year of publication
1996
Pages
6531 - 6534
Database
ISI
SICI code
0040-4039(1996)37:36<6531:SOOACB>2.0.ZU;2-1
Abstract
Optically active alpha-hydroxy ketones and esters have been prepared b y (salen)Mn(III)-catalyzed asymmetric oxidation of silyl enol ethers a nd silyl ketene acetals in high enantioselectivity, with ee values up to 81% for the alpha-hydroxy ketons and up to 57% for alpha-hydroxy es ters. The extent of conversion and the enantioselectivity depends stro ngly on the type of oxygen donor, the pH of the aqueous bleach medium, the additive, and the substitution pattern at the enol functionality. Copyright (C) 1996 Elsevier Science Ltd