Cyanoesterification of 1,2-dienes:: Synthesis and transformations of highly functionalized α-cyanomethylacrylate esters

被引：90

作者：

Nakao, Yoshiaki ^{[1
]}

Hirata, Yasuhiro ^{[1
]}

Hiyama, Tamejiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 23期

关键词：

D O I：

10.1021/ja0606834

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ni/PMe2Ph catalyst is found to effect regioselective addition of cyanoformate esters across 1,2-dienes, giving rise to 3-alkoxycarbonyl-3-butenenitriles. Functional groups such as cyano, protected hydroxyl, and amino groups in the 1,2-diene substrates are tolerated. Isomerization of the initial products to thermodynamically more stable isomers takes place possibly through further oxidative addition of the C-CN bond of 3-alkoxycarbonyl-3-butenenitriles to Ni(0) followed by reductive elimination. The cyanoesterification products undergo further addition across alkynes in the presence of a Ni/P(4-CF3-C6H4)3 catalyst. Copyright © 2006 American Chemical Society.

引用

页码：7420 / 7421

页数：2

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