Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis

A diastereo- and enantioselective approach to access chiral CF(2)-functionalized aziridines from difluorodiazoethyl phenyl sulfone (PhSO(2)CF(2)CHN(2)) and in situ-formed aldimines is described. This multicomponent reaction is enabled by a combined strong Brønsted acid catalytic platform consisting...

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Detalles Bibliográficos
Autores principales: Tan, Xing-Fa, Zhang, Fa-Guang, Ma, Jun-An
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155912/
https://www.ncbi.nlm.nih.gov/pubmed/32318120
http://dx.doi.org/10.3762/bjoc.16.60
Descripción
Sumario:A diastereo- and enantioselective approach to access chiral CF(2)-functionalized aziridines from difluorodiazoethyl phenyl sulfone (PhSO(2)CF(2)CHN(2)) 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 CF(2)-substituted aziridines could be further improved by a practical dissolution–filtration procedure.

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