Asymmetric synthesis of the Japanese beetle pheromone via boronic esters

被引：20

作者：

Hiscox, WC ^{[1
]}

Matteson, DS ^{[1
]}

机构：

[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2000年 / 614卷

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

boronic ester; asymmetric; propargylborane; pheromone;

D O I：

10.1016/S0022-328X(00)00595-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The pheromone of the Japanese beetle, [R-(Z)]-5-(1-decenyl)dihydro-2(3H)-furanone (7), has been synthesized efficiently in high enantiomeric purity via 1,2-dicyclohexyl-1,2-ethanediol boronic esters. The synthetic route involves reaction of an alpha -chloro boronic ester with an alkynyllithium, and provides the first successful example of this substitution process in an asymmetric synthesis. (C) 2000 Elsevier Science B.V. All rights reserved.

引用

页码：314 / 317

页数：4

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