邻二烷基阵列的催化对映选择性合成。

Catalytic enantioselective synthesis of vicinal dialkyl arrays.

作者信息

van Zijl Anthoni W, Szymanski Wiktor, López Ferrnando, Minnaard Adriaan J, Feringa Ben L

机构信息

Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen, Nijenborgh 4, 9747AG, Groningen, The Netherlands.

出版信息

J Org Chem. 2008 Sep 19;73(18):6994-7002. doi: 10.1021/jo8010649. Epub 2008 Aug 7.

DOI:10.1021/jo8010649

PMID:18683977

Abstract

With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.

摘要

采用连续的“不对称烯丙基烷基化（AAA）/交叉复分解反应（CM）/共轭加成（CA）”方案，可以以优异的立体选择性合成含有邻位二烷基排列的化合物的任意一种立体异构体。该方案在天然产物合成中的多功能性在蚂蚁信息素法那醇和拉西奥醇的制备中得到了证明。