An organocatalytic enantioselective ring-reorganization domino sequence of methyleneindolinones with 2-aminomalonates

Ji-Wei Ren; Zhen-Zhen Xie; Lan Zheng; Zhi-Peng Ye; Zhi-Xiong Deng; Qing-Lan Zhao; Jun-An Xiao; Kai Chen; Hao-Yue Xiang; Xiao-Qing Chen; Hua Yang

doi:10.1039/D0QO01364A

An organocatalytic enantioselective ring-reorganization domino sequence of methyleneindolinones with 2-aminomalonates†

Ji-Wei Ren,‡^ab Zhen-Zhen Xie,‡^a Lan Zheng,^a Zhi-Peng Ye,^a Zhi-Xiong Deng,^a Qing-Lan Zhao,^a Jun-An Xiao,

^c Kai Chen,

*^a Hao-Yue Xiang,

*^a Xiao-Qing Chen

^a and Hua Yang

*^a

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* Corresponding authors

^a College of Chemistry and Chemical Engineering, Central South University, Changsha, P. R. China
E-mail: hyangchem@csu.edu.cn, xianghaoyue@csu.edu.cn, kaichen@csu.edu.cn

^b Institute of Drug Discovery Technology, Ningbo University, Ningbo, Zhejiang, P. R. China

^c College of Chemistry and Materials Science, Nanning Normal University, Nanning, Guangxi, P. R. China

Abstract

An organocatalytic enantioselective ring-reorganization domino sequence (Michael addition/intramolecular ring-opening/lactamization) of methyleneindolinones with 2-aminomalonates has been established in this work. As a result, pyrrolo[3,4-c]quinolinones bearing two to three contiguous chiral centers were efficiently assembled in high yields (up to 92%) with excellent diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to >99% ee).

Organic Chemistry Frontiers

An organocatalytic enantioselective ring-reorganization domino sequence of methyleneindolinones with 2-aminomalonates†

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An organocatalytic enantioselective ring-reorganization domino sequence of methyleneindolinones with 2-aminomalonates

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