Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach

A 1,3‐aminothiolation was realized by reacting 2‐substituted cyclopropane 1,1‐dicarboxylates with sulfonamides and N‐(arylthio)succinimides. Under Sn(OTf)(2) catalysis the transformation proceeded smoothly to the corresponding ring‐opened products bearing the sulfonamide in the 1‐position next to th...

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Autores principales: Augustin, André U., Jones, Peter G., Werz, Daniel B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6771889/
https://www.ncbi.nlm.nih.gov/pubmed/31282001
http://dx.doi.org/10.1002/chem.201902160
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author Augustin, André U.
Jones, Peter G.
Werz, Daniel B.
author_facet Augustin, André U.
Jones, Peter G.
Werz, Daniel B.
author_sort Augustin, André U.
collection PubMed
description A 1,3‐aminothiolation was realized by reacting 2‐substituted cyclopropane 1,1‐dicarboxylates with sulfonamides and N‐(arylthio)succinimides. Under Sn(OTf)(2) catalysis the transformation proceeded smoothly to the corresponding ring‐opened products bearing the sulfonamide in the 1‐position next to the donor and the arylthio residue in the 3‐position next to the acceptor. The procedure was extended to the corresponding selenium analogues by employing N‐(phenylseleno)succinimides as an electrophilic selenium source.
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spelling pubmed-67718892019-10-07 Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach Augustin, André U. Jones, Peter G. Werz, Daniel B. Chemistry Communications A 1,3‐aminothiolation was realized by reacting 2‐substituted cyclopropane 1,1‐dicarboxylates with sulfonamides and N‐(arylthio)succinimides. Under Sn(OTf)(2) catalysis the transformation proceeded smoothly to the corresponding ring‐opened products bearing the sulfonamide in the 1‐position next to the donor and the arylthio residue in the 3‐position next to the acceptor. The procedure was extended to the corresponding selenium analogues by employing N‐(phenylseleno)succinimides as an electrophilic selenium source. John Wiley and Sons Inc. 2019-08-07 2019-09-06 /pmc/articles/PMC6771889/ /pubmed/31282001 http://dx.doi.org/10.1002/chem.201902160 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Augustin, André U.
Jones, Peter G.
Werz, Daniel B.
Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
title Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
title_full Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
title_fullStr Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
title_full_unstemmed Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
title_short Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
title_sort ring‐opening 1,3‐aminochalcogenation of donor–acceptor cyclopropanes: a three‐component approach
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6771889/
https://www.ncbi.nlm.nih.gov/pubmed/31282001
http://dx.doi.org/10.1002/chem.201902160
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