Synthesis of optically active 1,3-dienes from alkenylstannanes by a combination of electro-oxidation and copper-mediated homocoupling reaction

被引：9

作者：

Itoh, T ^{[1
]}

Emoto, S ^{[1
]}

Kondo, M ^{[1
]}

Ohara, H ^{[1
]}

Tanaka, H ^{[1
]}

Torii, S ^{[1
]}

机构：

[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN

来源：

ELECTROCHIMICA ACTA | 1997年 / 42卷 / 13-14期

关键词：

vinylstannanes; Cu-mediated reaction; electro-oxidation; optically active 1,3-diene;

D O I：

10.1016/S0013-4686(97)85490-4

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

A combination of electro-oxidation and copper(II) chloride mediated homocoupling of gamma-acyloxyvinylstannanes afforded 1,3-dienes. The stereoselectivity strongly depended on the solvent system and no isomerization occurred when the reactions were carried out in DMF (0.01 M). The facile synthesis of(6R, 11R)-(7E, 9E)-6,11-hexadeca-7,9-dienyl dibenzoate was thus accomplished from (R)-(E)-1-tributylstannyl-1-octene-3-ol, which was prepared through the lipase-catalyzed reaction in an optically pure form. (C) 1997 Elsevier Science Ltd.

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页码：2133 / 2142

页数：10

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