Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines

We present (3+2)‐ and (4+2)‐cycloadditions of donor–acceptor (D–A) cyclopropanes and cyclobutanes with N‐sulfinylamines and a sulfur diimide, along with a one‐pot, two‐step strategy for the formal insertion of HNSO(2) into D–A cyclopropanes. These are rare examples of cycloadditions with D–A cyclopr...

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Autores principales: Oliver, Gwyndaf A., Loch, Maximilian N., Augustin, André U., Steinbach, Pit, Sharique, Mohammed, Tambar, Uttam K., Jones, Peter G., Bannwarth, Christoph, Werz, Daniel B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9298015/
https://www.ncbi.nlm.nih.gov/pubmed/34499800
http://dx.doi.org/10.1002/anie.202106596
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author Oliver, Gwyndaf A.
Loch, Maximilian N.
Augustin, André U.
Steinbach, Pit
Sharique, Mohammed
Tambar, Uttam K.
Jones, Peter G.
Bannwarth, Christoph
Werz, Daniel B.
author_facet Oliver, Gwyndaf A.
Loch, Maximilian N.
Augustin, André U.
Steinbach, Pit
Sharique, Mohammed
Tambar, Uttam K.
Jones, Peter G.
Bannwarth, Christoph
Werz, Daniel B.
author_sort Oliver, Gwyndaf A.
collection PubMed
description We present (3+2)‐ and (4+2)‐cycloadditions of donor–acceptor (D–A) cyclopropanes and cyclobutanes with N‐sulfinylamines and a sulfur diimide, along with a one‐pot, two‐step strategy for the formal insertion of HNSO(2) into D–A cyclopropanes. These are rare examples of cycloadditions with D–A cyclopropanes and cyclobutanes whereby the 2π component consists of two different heteroatoms, thus leading to five‐ and six‐membered rings containing adjacent heteroatoms.
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spelling pubmed-92980152022-07-21 Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines Oliver, Gwyndaf A. Loch, Maximilian N. Augustin, André U. Steinbach, Pit Sharique, Mohammed Tambar, Uttam K. Jones, Peter G. Bannwarth, Christoph Werz, Daniel B. Angew Chem Int Ed Engl Research Articles We present (3+2)‐ and (4+2)‐cycloadditions of donor–acceptor (D–A) cyclopropanes and cyclobutanes with N‐sulfinylamines and a sulfur diimide, along with a one‐pot, two‐step strategy for the formal insertion of HNSO(2) into D–A cyclopropanes. These are rare examples of cycloadditions with D–A cyclopropanes and cyclobutanes whereby the 2π component consists of two different heteroatoms, thus leading to five‐ and six‐membered rings containing adjacent heteroatoms. John Wiley and Sons Inc. 2021-10-29 2021-12-01 /pmc/articles/PMC9298015/ /pubmed/34499800 http://dx.doi.org/10.1002/anie.202106596 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Oliver, Gwyndaf A.
Loch, Maximilian N.
Augustin, André U.
Steinbach, Pit
Sharique, Mohammed
Tambar, Uttam K.
Jones, Peter G.
Bannwarth, Christoph
Werz, Daniel B.
Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines
title Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines
title_full Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines
title_fullStr Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines
title_full_unstemmed Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines
title_short Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines
title_sort cycloadditions of donor–acceptor cyclopropanes and ‐butanes using s=n‐containing reagents: access to cyclic sulfinamides, sulfonamides, and sulfinamidines
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9298015/
https://www.ncbi.nlm.nih.gov/pubmed/34499800
http://dx.doi.org/10.1002/anie.202106596
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