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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...

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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
Descripción
Sumario: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.