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  α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation

Jia, H., & Ritter, T. (2022). α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation. Angewandte Chemie International Edition, 61(39): e202208978. doi:10.1002/anie.202208978.

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 Creators:
Jia, Hao1, Author           
Ritter, Tobias1, Author           
Affiliations:
1Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040308              

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Free keywords: Amino Acids; Carbocation; Carbonyl Compounds; Michael Acceptor; Umpolung
 Abstract: 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 Cα-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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Language(s): eng - English
 Dates: 2022-06-202022-07-272022-09-26
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202208978
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 61 (39) Sequence Number: e202208978 Start / End Page: - Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851