Beilstein Journal of Organic Chemistry (Apr 2020)

Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis

  • Xing-Fa Tan,
  • Fa-Guang Zhang,
  • Jun-An Ma

DOI
https://doi.org/10.3762/bjoc.16.60
Journal volume & issue
Vol. 16, no. 1
pp. 638 – 644

Abstract

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A diastereo- and enantioselective approach to access chiral CF2-functionalized aziridines from difluorodiazoethyl phenyl sulfone (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 the obtained CF2-substituted aziridines could be further improved by a practical dissolution–filtration procedure.

Keywords