DIRECT OXYFUNCTIONALIZATION AT UNACTIVATED SITES - SYNTHESIS OF 5-BETA-HYDROXYSTEROIDS BY PERFLUORODIALKYLOXAZIRIDINES

Citation
A. Arnone et al., DIRECT OXYFUNCTIONALIZATION AT UNACTIVATED SITES - SYNTHESIS OF 5-BETA-HYDROXYSTEROIDS BY PERFLUORODIALKYLOXAZIRIDINES, Journal of organic chemistry, 59(19), 1994, pp. 5511-5513
Citations number
56
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
59
Issue
19
Year of publication
1994
Pages
5511 - 5513
Database
ISI
SICI code
0022-3263(1994)59:19<5511:DOAUS->2.0.ZU;2-L
Abstract
By treatment with perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 1a, 5 beta-steroids 2a-i (belonging to different classes, such as androstane s, cholestanes, pregnanes, and cholanic acids) have been hydroxylated in good yields and with complete site selectivity and stereoselectivit y to corresponding 5 beta-hydroxy derivatives 3a-i independently from the presence of halide, ketone, carboxylic acid, and ester moieties on C-3, C-11, C-12, C-17, C-20, C-21, and C-24.