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α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation
Here we report an α‐thianthrenium carbonyl species, as the equivalent of an α‐carbonyl carbocation, which is generated by the radical conjugate addition of a trifluoromethyl thianthrenium salt to Michael acceptors. The reactivity allows for the synthesis of C(α)‐tetrasubstituted α‐ and β‐amino acid...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804271/ https://www.ncbi.nlm.nih.gov/pubmed/35895980 http://dx.doi.org/10.1002/anie.202208978 |
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author | Jia, Hao Ritter, Tobias |
author_facet | Jia, Hao Ritter, Tobias |
author_sort | Jia, Hao |
collection | PubMed |
description | Here we report an α‐thianthrenium carbonyl species, as the equivalent of an α‐carbonyl carbocation, which is generated by the radical conjugate addition of a trifluoromethyl thianthrenium salt to Michael acceptors. The reactivity allows for the synthesis of C(α)‐tetrasubstituted α‐ and β‐amino acid analogues via a Ritter reaction by addition of acetonitrile. Addition of hydroxide, methoxide, and even fluoride can afford α‐heteroatom substituted α‐phenylpropanoates. |
format | Online Article Text |
id | pubmed-9804271 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-98042712023-01-03 α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation Jia, Hao Ritter, Tobias Angew Chem Int Ed Engl Communications Here we report an α‐thianthrenium carbonyl species, as the equivalent of an α‐carbonyl carbocation, which is generated by the radical conjugate addition of a trifluoromethyl thianthrenium salt to Michael acceptors. The reactivity allows for the synthesis of C(α)‐tetrasubstituted α‐ and β‐amino acid analogues via a Ritter reaction by addition of acetonitrile. Addition of hydroxide, methoxide, and even fluoride can afford α‐heteroatom substituted α‐phenylpropanoates. John Wiley and Sons Inc. 2022-08-19 2022-09-26 /pmc/articles/PMC9804271/ /pubmed/35895980 http://dx.doi.org/10.1002/anie.202208978 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://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 Jia, Hao Ritter, Tobias α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation |
title | α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation |
title_full | α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation |
title_fullStr | α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation |
title_full_unstemmed | α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation |
title_short | α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation |
title_sort | α‐thianthrenium carbonyl species: the equivalent of an α‐carbonyl carbocation |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804271/ https://www.ncbi.nlm.nih.gov/pubmed/35895980 http://dx.doi.org/10.1002/anie.202208978 |
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