RH-MEDIATED CYCLOPENTANE CONSTRUCTION CAN COMPETE WITH BETA-HYDRIDE ELIMINATION - SYNTHESIS OF (+/-)-TOCHUINYL ACETATE

被引：122

作者：

TABER, DF

HENNESSY, MJ

LOUEY, JP

机构：

[1] Department of Chemistry and Biochemistry, University of Delaware, Newark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 02期

关键词：

D O I：

10.1021/jo00028a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with beta-hydride elimination, except when the beta-hydrogen is ternary. Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-tochuinyl acetate 25. Both the cyclization to form 28 and the alkylation of 28 proceed with remarkable diastereoselectivity.

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页码：436 / 441

页数：6

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