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

被引：23

作者：

CURCI, R

D'ACCOLTI, L

DETOMASO, A

FUSCO, C

TAKEUCHI, K

OHGA, Y

EATON, PE

YIP, YC

机构：

[1] KYOTO UNIV, FAC ENGN, DEPT HYDROCARBON CHEM, SAKYO KU, KYOTO 60601, JAPAN

[2] UNIV CHICAGO, DEPT CHEM, CHICAGO, IL 60637 USA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 28期

关键词：

DIOXIRANES; OXYGEN INSERTION; 1,2-DIOLS; OXIDATION; ALPHA-HYDROXY KETONES;

D O I：

10.1016/0040-4039(93)88085-W

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding alpha-hydroxy ketones in high 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.

引用

收藏

页码：4559 / 4562

页数：4

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