Organocatalytic Diastereo- and Enantioselective Synthesis of Chlorinated and Trifluoromethylated Pyrrolidines Featuring a Removable Nitro Group

Xiaoze Bao; Mengyuan Wu; Guishun Bai; Xusheng Duan; Jiangwei Pan; Yang Yang; Zeyu Wang; Xuanrong Sun; Jean Rodriguez; Damien Bonne; Hong Wang

doi:10.1021/acs.orglett.5c02233

Organocatalytic Diastereo- and Enantioselective Synthesis of Chlorinated and Trifluoromethylated Pyrrolidines Featuring a Removable Nitro Group

Org Lett. 2025 Jul 25;27(29):7908-7913. doi: 10.1021/acs.orglett.5c02233. Epub 2025 Jul 14.

Authors

Xiaoze Bao^{1

2}, Mengyuan Wu¹, Guishun Bai¹, Xusheng Duan¹, Jiangwei Pan¹, Yang Yang¹, Zeyu Wang², Xuanrong Sun¹, Jean Rodriguez³, Damien Bonne³, Hong Wang^{1

2}

Affiliations

¹ College of Pharmaceutical Science and Collaborative Innovation Centre of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014 China.
² Binjiang Institute of Artificial Intelligence, ZJUT, Hangzhou 310056, China.
³ Aix Marseille Univ, CNRS, Centrale Med, iSm2, Marseille 13397, France.

PMID: 40658758
DOI: 10.1021/acs.orglett.5c02233

Abstract

A new concept was reported to use nitro as a removable activating group for the stereoselective construction of chlorinated stereogenic centers. This was proven by the enantioselective (3 + 2) cycloaddition of isatin-derived 1,3-dipoles and chloronitroalkenes, affording a series of spiro-oxindoles featuring four consecutive stereogenic centers including one that is chlorinated.