ASYMMETRIC BAEYER-VILLIGER REACTION - DIASTEREODIFFERENTIATING PERACID OXIDATION OF CHIRAL ACETAL IN THE PRESENCE OF LEWIS-ACID

Authors
SUGIMURA T FUJIWARA Y TAI A
Citation
T. Sugimura et al., ASYMMETRIC BAEYER-VILLIGER REACTION - DIASTEREODIFFERENTIATING PERACID OXIDATION OF CHIRAL ACETAL IN THE PRESENCE OF LEWIS-ACID, Tetrahedron letters, 38(34), 1997, pp. 6019-6022
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
34
Year of publication
1997
Pages
6019 - 6022
Database
ISI
SICI code
0040-4039(1997)38:34<6019:ABR-DP>2.0.ZU;2-D
Abstract
Oxidation of 2 with m-chloroperbenzoic acid in the presence of SnCl4 a t -78 degrees C followed by hydrolysis afforded optically active 4 in a quantitative yield. The enantiomeric excess tee) of 4 largely depend ed on the reaction solvent, the chiral diol part, the Lewis acid and i ts amount. The best ee was 89% when 2 (R = Ph) having 2,4-pentanediol was oxidized at -100 degrees C. (C) 1997 Elsevier Science Ltd.