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Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives
A modular and waste‐free strategy for constructing N‐substituted cyclic amines via decarboxylative N‐alkylation of α‐amino acids employing ruthenium‐ and iron‐based catalysts is presented. The reported method allows the synthesis of a wide range of five‐ and six‐membered N‐alkylated heterocycles in...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6772061/ https://www.ncbi.nlm.nih.gov/pubmed/31328892 http://dx.doi.org/10.1002/cssc.201901499 |
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author | Afanasenko, Anastasiia Hannah, Rachael Yan, Tao Elangovan, Saravanakumar Barta, Katalin |
author_facet | Afanasenko, Anastasiia Hannah, Rachael Yan, Tao Elangovan, Saravanakumar Barta, Katalin |
author_sort | Afanasenko, Anastasiia |
collection | PubMed |
description | A modular and waste‐free strategy for constructing N‐substituted cyclic amines via decarboxylative N‐alkylation of α‐amino acids employing ruthenium‐ and iron‐based catalysts is presented. The reported method allows the synthesis of a wide range of five‐ and six‐membered N‐alkylated heterocycles in moderate‐to‐excellent yields starting from predominantly proline and a broad range of benzyl alcohols, and primary and secondary aliphatic alcohols. Examples using pipecolic acid for the construction of piperidine derivatives, as well as the one‐pot synthesis of α‐amino nitriles, are also shown. |
format | Online Article Text |
id | pubmed-6772061 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-67720612019-10-07 Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives Afanasenko, Anastasiia Hannah, Rachael Yan, Tao Elangovan, Saravanakumar Barta, Katalin ChemSusChem Full Papers A modular and waste‐free strategy for constructing N‐substituted cyclic amines via decarboxylative N‐alkylation of α‐amino acids employing ruthenium‐ and iron‐based catalysts is presented. The reported method allows the synthesis of a wide range of five‐ and six‐membered N‐alkylated heterocycles in moderate‐to‐excellent yields starting from predominantly proline and a broad range of benzyl alcohols, and primary and secondary aliphatic alcohols. Examples using pipecolic acid for the construction of piperidine derivatives, as well as the one‐pot synthesis of α‐amino nitriles, are also shown. John Wiley and Sons Inc. 2019-07-22 2019-08-22 /pmc/articles/PMC6772061/ /pubmed/31328892 http://dx.doi.org/10.1002/cssc.201901499 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Full Papers Afanasenko, Anastasiia Hannah, Rachael Yan, Tao Elangovan, Saravanakumar Barta, Katalin Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives |
title | Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives |
title_full | Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives |
title_fullStr | Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives |
title_full_unstemmed | Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives |
title_short | Ruthenium and Iron‐Catalysed Decarboxylative N‐alkylation of Cyclic α‐Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives |
title_sort | ruthenium and iron‐catalysed decarboxylative n‐alkylation of cyclic α‐amino acids with alcohols: sustainable routes to pyrrolidine and piperidine derivatives |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6772061/ https://www.ncbi.nlm.nih.gov/pubmed/31328892 http://dx.doi.org/10.1002/cssc.201901499 |
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