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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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
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author Tan, Xing-Fa
Zhang, Fa-Guang
Ma, Jun-An
author_facet Tan, Xing-Fa
Zhang, Fa-Guang
Ma, Jun-An
author_sort Tan, Xing-Fa
collection PubMed
description 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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spelling pubmed-71559122020-04-21 Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis Tan, Xing-Fa Zhang, Fa-Guang Ma, Jun-An Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2020-04-07 /pmc/articles/PMC7155912/ /pubmed/32318120 http://dx.doi.org/10.3762/bjoc.16.60 Text en Copyright © 2020, Tan et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tan, Xing-Fa
Zhang, Fa-Guang
Ma, Jun-An
Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis
title Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis
title_full Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis
title_fullStr Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis
title_full_unstemmed Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis
title_short Asymmetric synthesis of CF(2)-functionalized aziridines by combined strong Brønsted acid catalysis
title_sort asymmetric synthesis of cf(2)-functionalized aziridines by combined strong brønsted acid catalysis
topic Full Research Paper
url 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
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