HIGHLY DIASTEREOSELECTIVE CONJUGATE ADDITION OF ORGANOCUPRATE TO ACYCLIC E-ENONES AND Z-ENONES - REVERSAL STEREOSELECTIVITY UNDER KINETIC AND THERMODYNAMIC CONDITIONS

被引：11

作者：

YAMAMOTO, K

YAMADA, S

YAMAGUCHI, K

机构：

[1] TOKYO MED & DENT UNIV,INST MED & DENT ENGN,SURUGADAI KANDA,CHIYODA KU,TOKYO 113,JAPAN

[2] SHOWA UNIV,SCH PHARMACEUT SCI,SHINAGAWA KU,TOKYO 142,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)60813-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gilman reagent (lithium dimethylcuprate) adds stereoselectively (98%) to (E)- and (Z)-steroidal 22-en-24-ones to yield 22R-methylated product regardless of the geometry of the enones. The same reagent adds with complete reversal selectivity to the (E)- and (Z)-enones in the presence of TMSCl to yield 22R- and 22S-methyl-24-ketones, respectively.

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页码：7521 / 7524

页数：4

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