Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes

α‐Amino acid derivatives are key components of the molecules of life. The synthesis of α‐amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we report a practical method for the preparation of α‐amino acid derivatives via direct hydrative amination of activate...

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Detalles Bibliográficos
Autores principales: Feng, Minghao, Tinelli, Roberto, Meyrelles, Ricardo, González, Leticia, Maryasin, Boris, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10098499/
https://www.ncbi.nlm.nih.gov/pubmed/36222199
http://dx.doi.org/10.1002/anie.202212399
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author Feng, Minghao
Tinelli, Roberto
Meyrelles, Ricardo
González, Leticia
Maryasin, Boris
Maulide, Nuno
author_facet Feng, Minghao
Tinelli, Roberto
Meyrelles, Ricardo
González, Leticia
Maryasin, Boris
Maulide, Nuno
author_sort Feng, Minghao
collection PubMed
description α‐Amino acid derivatives are key components of the molecules of life. The synthesis of α‐amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we report a practical method for the preparation of α‐amino acid derivatives via direct hydrative amination of activated alkynes under mild conditions, relying on sulfinamides as the nitrogen source. Computational studies suggest that the reaction is enabled by a new type of sulfonium [2,3]‐sigmatropic rearrangement.
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spelling pubmed-100984992023-04-14 Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes Feng, Minghao Tinelli, Roberto Meyrelles, Ricardo González, Leticia Maryasin, Boris Maulide, Nuno Angew Chem Int Ed Engl Communications α‐Amino acid derivatives are key components of the molecules of life. The synthesis of α‐amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we report a practical method for the preparation of α‐amino acid derivatives via direct hydrative amination of activated alkynes under mild conditions, relying on sulfinamides as the nitrogen source. Computational studies suggest that the reaction is enabled by a new type of sulfonium [2,3]‐sigmatropic rearrangement. John Wiley and Sons Inc. 2022-11-29 2023-01-02 /pmc/articles/PMC10098499/ /pubmed/36222199 http://dx.doi.org/10.1002/anie.202212399 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Feng, Minghao
Tinelli, Roberto
Meyrelles, Ricardo
González, Leticia
Maryasin, Boris
Maulide, Nuno
Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes
title Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes
title_full Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes
title_fullStr Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes
title_full_unstemmed Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes
title_short Direct Synthesis of α‐Amino Acid Derivatives by Hydrative Amination of Alkynes
title_sort direct synthesis of α‐amino acid derivatives by hydrative amination of alkynes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10098499/
https://www.ncbi.nlm.nih.gov/pubmed/36222199
http://dx.doi.org/10.1002/anie.202212399
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