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通过铑迁移策略立体选择性合成乙烯基环丙[a]吲哚啉

Stereoselective Synthesis of Vinylcyclopropa[]indolines via a Rh-Migration Strategy.

作者信息

Guo Pan, Sun Wangbin, Liu Yu, Li Yong-Xin, Loh Teck-Peng, Jiang Yaojia

机构信息

Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616.

出版信息

Org Lett. 2020 Aug 7;22(15):5978-5983. doi: 10.1021/acs.orglett.0c02071. Epub 2020 Jul 16.

Abstract

A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes . By employing a Rh-migration strategy, the products can be obtained with good to excellent : ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

摘要

已开发出一种温和的铑催化体系,通过吲哚与环丙烯开环生成的乙烯基类卡宾进行环丙烷化反应来合成乙烯基环丙[a]吲哚啉。通过采用铑迁移策略,可以以良好至优异的比例(≤99:1)和完全的非对映选择性(≤99:1)获得产物。该方法操作简便,催化剂用量低,适用于多种官能团。

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