Synthesis of aziridines with multiple chiral substitutions by copper-catalyzed diastereoselective radical aminotrifluoromethylation of alkenes

Shuanglin Qin, Linbin Yao, Yunhao Luo, Tongtong Liu, Jiayuan Xu, Yue Sun, Ning Wang, Jun Yan, Bencan Tang, Guang Yang, Cheng Yang

Research output: Journal PublicationArticlepeer-review

6 Citations (Scopus)

Abstract

A one-step catalytic and diastereoselective method for the synthesis of aziridines possessing multiple chiral substitutions by radical aminotrifluoromethylation of alkenes has been developed for the first time. The reaction utilizes a Cu(i)/l-proline complex as a catalyst and a chiral sulfinamide group performs the role of nucleophile and chiral directing group. This synthetic strategy provides one-step access to a wide variety of substituted aziridines with good chemical yield, excellent diastereoselectivity and broad functional group tolerance. A possible reaction mechanism is proposed based on DFT calculations. The method should be useful for the rapid synthesis of chiral CF3-containing building blocks and novel drug molecules.

Original languageEnglish
Pages (from-to)3132-3136
Number of pages5
JournalOrganic Chemistry Frontiers
Volume7
Issue number20
DOIs
Publication statusPublished - 21 Oct 2020

ASJC Scopus subject areas

  • Organic Chemistry

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