SELECTIVE OXIDATION OF TERTIARY-SECONDARY VIC-DIOLS TO ALPHA-HYDROXY KETONES BY DIOXIRANES

Authors
CURCI R DACCOLTI L DETOMASO A FUSCO C TAKEUCHI K OHGA Y EATON PE YIP YC
Citation
R. Curci et al., SELECTIVE OXIDATION OF TERTIARY-SECONDARY VIC-DIOLS TO ALPHA-HYDROXY KETONES BY DIOXIRANES, Tetrahedron letters, 34(28), 1993, pp. 4559-4562
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
28
Year of publication
1993
Pages
4559 - 4562
Database
ISI
SICI code
0040-4039(1993)34:28<4559:SOOTVT>2.0.ZU;2-I
Abstract
Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane ( 1b) efficiently afford the conversion of bicyclic diols bicyclo(2.2.2] octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols ad amantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentapr ismane-3,4-diol (5) into the corresponding alpha-hydroxy ketones in hi gh yields and under mild conditions. In the oxidation of (+)-pinane-2, 3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield >97% with retention of configuration.