高非对映选择性合成多取代环丙甲腈通过钯催化氰酯化环丙烯。

Highly Diastereoselective Synthesis of Polysubstituted Cyclopropanecarbonitriles via Palladium-Catalyzed Cyanoesterification of Cyclopropenes.

机构信息

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, 2318 Yuhangtang Road, Hangzhou 311121, China.

出版信息

Org Lett. 2023 Jul 14;25(27):5128-5133. doi: 10.1021/acs.orglett.3c01875. Epub 2023 Jul 6.

DOI:10.1021/acs.orglett.3c01875

PMID:37409772

Abstract

We herein develop a highly diastereoselective synthesis of cyano-substituted cyclopropanes via palladium-catalyzed direct cyanoesterification of cyclopropenes, which features mild reaction conditions, good functional group compatibility, and simple operation. This transformation represents a stepwise, highly atom economic, and scalable protocol for obtaining synthetically useful cyclopropanecarbonitriles.

摘要

我们在此开发了一种通过钯催化的环丙烯直接氰酯化反应来合成氰基取代的环丙烷的高度非对映选择性合成方法，该方法具有反应条件温和、官能团兼容性好、操作简单等特点。这种转化代表了一种逐步的、高度原子经济性和可扩展的获得合成有用的环丙烷腈的方法。