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通过吲哚与乙烯基锍盐的N-H官能化实现吡咯并喹啉的非对映选择性合成。

Diastereoselective Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles with Vinyl Sulfonium Salts.

作者信息

Ma Ruiying, Zhou Zijie, Yang Peng, Ye Ling, Shi Zhichuan, Zhao Zhigang, Li Xuefeng

机构信息

Key Laboratory of General Chemistry of the National Ethnic Affairs Commission, School of Chemistry and Environment, Southwest Minzu University, Chengdu 610041, China.

Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China.

出版信息

J Org Chem. 2024 Jan 5;89(1):452-462. doi: 10.1021/acs.joc.3c02211. Epub 2023 Dec 12.

DOI:10.1021/acs.joc.3c02211
PMID:38085572
Abstract

A [2 + 4]/[1 + 2] annulation approach was successfully established to construct pyrroloquinoline-fused cyclopropane in a highly diastereoselective fashion (>20:1 dr). The tetracyclic 1,7-fused indoles were efficiently obtained from readily available starting materials under mild conditions. This methodology displays impressive substrate generality with two reaction components. The products resulting from this doubly annulative strategy are useful synthetic intermediates.

摘要

成功建立了一种[2 + 4]/[1 + 2]环化方法,以高非对映选择性方式(>20:1 dr)构建吡咯并喹啉稠合环丙烷。在温和条件下,从容易获得的起始原料高效地得到了四环1,7-稠合吲哚。该方法对两种反应组分显示出令人印象深刻的底物通用性。这种双重环化策略产生的产物是有用的合成中间体。

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