Asymmetric Synthesis of CF2-Aziridines Enabled by Combined Strong Brønsted Acid Catalysis

Submitting author affiliation:
Tianjin University, Tianjin, China

Beilstein Arch. 2020, 202020.

Published 17 Feb 2020

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A diastereo- and enantioselective approach to access chiral CF2-functionalized aziridines from phenylsulfone difluorodiazoethane (PhSO2CF2CHN2) and in-situ formed aldimines is described. This multicomponent reaction is enabled by a combined strong Brønsted acid catalytic platform consisting of a chiral disulfonimide and 2-carboxyphenylboronic acid. The optical purity of obtained CF2-aziridines could be further improved by a practical dissolution-filtration procedure.

Keywords: difluoromethyl compounds; aziridines; fluorinated diazo reagents; chiral disulfonimides; strong Brønsted acids

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Tan, X.-F.; Zhang, F.-G.; Ma, J.-A. Beilstein Arch. 2020, 202020. doi:10.3762/bxiv.2020.20.v1

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