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

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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.

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

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Article information


Submitted
17 May 2020
Accepted
22 Jun 2020
First published
24 Jun 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

S. Qin, L. Yao, Y. Luo, T. Liu, J. Xu, Y. Sun, N. Wang, J. Yan, B. Tang, G. Yang and C. Yang, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00603C

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