手性烯丙醇与偕二锌卡宾体的非对映选择性锌环丙烷化反应。

Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids.

作者信息

Fournier Jean-François, Mathieu Simon, Charette André B

机构信息

Département de Chimie, Université de Montréal, Montréal, Québec, Canada H3C 3J7.

出版信息

J Am Chem Soc. 2005 Sep 28;127(38):13140-1. doi: 10.1021/ja054328+.

DOI:10.1021/ja054328+

Abstract

The highly diastereoselective zinco-cyclopropanation of chiral allylic alcohols using gem-dizinc carbenoids is described. The reaction produces three contiguous stereogenic centers, and the resulting chiral cyclopropylzinc derivatives can be trapped with electrophiles with retention of configuration. Simple functional group manipulations lead to the efficient synthesis of orthogonally protected 1,2,3-substituted cyclopropane derivatives.

摘要

描述了使用偕二锌类卡宾对手性烯丙醇进行高度非对映选择性锌环丙烷化反应。该反应产生三个相邻的立体ogenic中心，并且所得的手性环丙基锌衍生物可以与亲电试剂捕获，构型保持不变。简单的官能团操作可实现对正交保护的1,2,3-取代环丙烷衍生物的高效合成。

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