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

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 chi...

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Main Authors:	Xing-Fa Tan, Fa-Guang Zhang, Jun-An Ma
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-04-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	aziridines chiral disulfonimides difluoromethyl compounds fluorinated diazo reagents strong brønsted acids
Online Access:	https://doi.org/10.3762/bjoc.16.60

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spelling	doaj-770de75ff35d4602abfc775cc3cd1e782021-04-02T10:01:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-04-0116163864410.3762/bjoc.16.601860-5397-16-60Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysisXing-Fa Tan0Fa-Guang Zhang1Jun-An Ma2Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, ChinaDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, ChinaDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, ChinaA 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.https://doi.org/10.3762/bjoc.16.60aziridineschiral disulfonimidesdifluoromethyl compoundsfluorinated diazo reagentsstrong brønsted acids
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Xing-Fa Tan Fa-Guang Zhang Jun-An Ma
spellingShingle	Xing-Fa Tan Fa-Guang Zhang Jun-An Ma Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis Beilstein Journal of Organic Chemistry aziridines chiral disulfonimides difluoromethyl compounds fluorinated diazo reagents strong brønsted acids
author_facet	Xing-Fa Tan Fa-Guang Zhang Jun-An Ma
author_sort	Xing-Fa Tan
title	Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis
title_short	Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis
title_full	Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis
title_fullStr	Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis
title_full_unstemmed	Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis
title_sort	asymmetric synthesis of cf2-functionalized aziridines by combined strong brønsted acid catalysis
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-04-01
description	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.
topic	aziridines chiral disulfonimides difluoromethyl compounds fluorinated diazo reagents strong brønsted acids
url	https://doi.org/10.3762/bjoc.16.60
work_keys_str_mv	AT xingfatan asymmetricsynthesisofcf2functionalizedaziridinesbycombinedstrongbrønstedacidcatalysis AT faguangzhang asymmetricsynthesisofcf2functionalizedaziridinesbycombinedstrongbrønstedacidcatalysis AT junanma asymmetricsynthesisofcf2functionalizedaziridinesbycombinedstrongbrønstedacidcatalysis
_version_	1724168090017595392

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

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