Asymmetric synthesis of CF<sub>2</sub>-functionalized aziridines by combined strong Brønsted acid catalysis.

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

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

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

Afiliación

Tan XF; Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, China.
Zhang FG; Joint School of NUS & TJU, International Campus of Tianjin University, Fuzhou 350207, China.
Ma JA; Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, China.

Beilstein J Org Chem ; 16: 638-644, 2020.

Article en En | MEDLINE | ID: mdl-32318120

ABSTRACT

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.

Palabras clave

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

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Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: Beilstein J Org Chem Año: 2020 Tipo del documento: Article País de afiliación: China