Novel isomerically pure tetrasubstituted allylboronates:: Stereocontrolled synthesis of α-exomethylene γ-lactones as aldol-like adducts with a stereogenic quaternary carbon center

被引：76

作者：

Kennedy, JWJ ^{[1
]}

Hall, DG ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 06期

关键词：

D O I：

10.1021/ja016391e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In spite of their inherent isomerization tendency and low reactivity, 1-alkoxycarbonyl vinylcopper(I) intermediates from the conjugate addition of organocuprates onto acetylenic esters were trapped with very high cis-addition selectivity with iodomethylboronic esters in the presence of HMPA. The resulting isomerically pure 3,3-disubstituted allylboronates react with aldehydes in a highly diastereo- and enantioselective manner, providing α-exomethylene γ-lactones with a stereogenic quaternary β-carbon center. Copyright © 2002 American Chemical Society.

引用

页码：898 / 899

页数：2

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