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

Xing-Fa Tan; Fa-Guang Zhang; Jun-An Ma

doi:10.3762/bjoc.16.60

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

Affiliations

Xing-Fa Tan: Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, China
Fa-Guang Zhang: Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, China
Jun-An Ma: Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, China

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.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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