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

ABSTRACT: 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.

SUBMITTER: Tan XF

PROVIDER: S-EPMC7155912 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Tan Xing-Fa XF Zhang Fa-Guang FG Ma Jun-An JA

Beilstein journal of organic chemistry 20200407

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 p ...[more]

PMID: 32318120

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