Ruthenium-catalyzed Oppenauer-type oxidation of 3 beta-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality

被引：63

作者：

Almeida, MLS ^{[1
]}

Kocovsky, P ^{[1
]}

Backvall, JE ^{[1
]}

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,LEICS,ENGLAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 19期

关键词：

D O I：

10.1021/jo960361q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of 5-unsaturated 3 beta-hydroxy steroids 1 to the corresponding 4-en-3-one derivatives 2 can be performed efficiently by acetone at reflux in the presence of a catalytic system consisting of either (PPh(3))(3)RuCl2 (3) and K2CO3 or [(C(4)Ph(4)COHOCC(4)Ph(4))(mu-H)][(CO)(4)Ru-2] (4). The reaction proceeds via a ruthenium-catalyzed dehydrogenation of 1 and subsequent hydrogen transfer to acetone with concomitant double bond migration.

引用

页码：6587 / 6590

页数：4

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