Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Afanasenko, Anastasiia, Hannah, Rachael, Yan, Tao, Elangovan, Saravanakumar, Barta, Katalin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
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
_version_ 1783455827518029824
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
work_keys_str_mv AT afanasenkoanastasiia rutheniumandironcatalyseddecarboxylativenalkylationofcyclicaaminoacidswithalcoholssustainableroutestopyrrolidineandpiperidinederivatives
AT hannahrachael rutheniumandironcatalyseddecarboxylativenalkylationofcyclicaaminoacidswithalcoholssustainableroutestopyrrolidineandpiperidinederivatives
AT yantao rutheniumandironcatalyseddecarboxylativenalkylationofcyclicaaminoacidswithalcoholssustainableroutestopyrrolidineandpiperidinederivatives
AT elangovansaravanakumar rutheniumandironcatalyseddecarboxylativenalkylationofcyclicaaminoacidswithalcoholssustainableroutestopyrrolidineandpiperidinederivatives
AT bartakatalin rutheniumandironcatalyseddecarboxylativenalkylationofcyclicaaminoacidswithalcoholssustainableroutestopyrrolidineandpiperidinederivatives