2019ChemSusChemOpen access

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

Anastasiia M. Afanasenko, Rachael Hannah, Tao Yan, Saravanakumar Elangovan, Katalin Barta

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Abstract

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.

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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.

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Available abstract

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.

Key concepts: Pyrrolidine, Alkylation, Piperidine, Chemistry, Ruthenium, Organic chemistry, Pipecolic acid, Catalysis

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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 — Research Paper | ScholarLens