通过环丙基甲醇与汞（II）盐开环反应实现聚丙酸酯单元和杂环化合物的立体选择性合成。

Stereoselective synthesis of polypropionate units and heterocyclic compounds by cyclopropylcarbinol ring-opening with mercury(II) salts.

作者信息

Meyer Christophe, Blanchard Nicolas, Defosseux Magali, Cossy Janine

机构信息

Laboratoire de Chimie Organique, associé au CNRS, ESPCI, 10 rue Vauquelin 75231 Paris Cedex 05, France.

出版信息

Acc Chem Res. 2003 Oct;36(10):766-72. doi: 10.1021/ar020154e.

DOI:10.1021/ar020154e

PMID:14567710

Abstract

The mercury(II)-mediated electrophilic ring-opening reaction of various cyclopropylcarbinol derivatives bearing adjacent stereocenters and a remote nucleophilic functional group provides a useful strategy for synthesizing compounds bearing several contiguous stereocenters. These highly diastereoselective reactions occur with anchimeric assistance by the internal nucleophilic moiety and afford synthetically valuable building blocks such as polypropionate units or heterocyclic compounds. The application of cyclopropylcarbinol ring-opening for the preparation of functionalized oxygen heterocycles in natural product synthesis is also outlined.

摘要

各种带有相邻立体中心和远程亲核官能团的环丙基甲醇衍生物的汞（II）介导的亲电开环反应，为合成含有多个相邻立体中心的化合物提供了一种有用的策略。这些高度非对映选择性反应在内部亲核部分的邻基参与作用下发生，并提供具有合成价值的结构单元，如聚丙酸酯单元或杂环化合物。还概述了环丙基甲醇开环在天然产物合成中用于制备功能化氧杂环的应用。