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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...

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Autores principales: Jia, Hao, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
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.
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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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