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Ruthenium and Iron-Catalysed Decarboxylative N-alkylation of Cyclic ?-Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives.

ABSTRACT: A modular and waste-free strategy for constructing N-substituted cyclic amines via decarboxylative N-alkylation of ?-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 ?-amino nitriles, are also shown.

SUBMITTER: Afanasenko A

PROVIDER: S-EPMC6772061 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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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.

Afanasenko Anastasiia A Hannah Rachael R Yan Tao T Elangovan Saravanakumar S Barta Katalin K

ChemSusChem 20190722 16

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 ...[more]

PMID: 31328892

Similar Datasets

Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles.

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Visible-Light-Enabled Direct Decarboxylative N-Alkylation.

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