Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA

被引：131

作者：

Donohoe, TJ

Blades, K

Moore, PR

Waring, MJ

Winter, JJG

Helliwell, M

Newcombe, NJ

Stemp, G

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

[2] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[3] AstraZeneca Pharmaceut, Macclesfield SK10 4TG, Cheshire, England

[4] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 23期

关键词：

D O I：

10.1021/jo026161y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OSO4 is presented and a plausible mechanism described.

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页码：7946 / 7956

页数：11

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