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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, A., Hannah, R., Yan, T., Elangovan, S. & Barta, K., 22-Aug-2019, In : Chemsuschem. 12, 16, p. 3801-3807 7 p.

Research output: Contribution to journalArticleAcademicpeer-review

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.

Original languageEnglish
Pages (from-to)3801-3807
Number of pages7
JournalChemsuschem
Volume12
Issue number16
Early online date22-Jul-2019
Publication statusPublished - 22-Aug-2019

    Keywords

  • AZOMETHINE YLIDES, BOND FORMATION, PROLINE, AMINATION, ACTIVATION, COMPLEXES, MECHANISM, PYRIDINE, OXIDE

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