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Abstract <p>In this work, we describe the synthesis of chiral (<i>R</i>)-(‒)-piperidine-2,4-dione derived from (<i>R</i>)-(‒)-phenylglycinol, a valuable building block for the diastereoselective synthesis of piperidine alkaloids. The key step involves intramolecular cyclization: when the electrophile is an ester, the reaction proceeds via the formation of a Grignard intermediate, whereas when the electrophile is a nitrile, the cyclization follows a Blaise-type mechanism.</p>

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Intramolecular Cyclization of Grignard or Blaise Intermediates for the Synthesis of a Chiral Piperidine-2,4-dione Derived from (R)-(‒)-Phenylglycinol

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • H. Rodríguez-Matsui,
  • A. Aguilar-Aguilar,
  • A. Carrasco-Carballo,
  • V. Carranza-Téllez,
  • A. Palillero-Cisneros,
  • J. R. Juárez Posadas,
  • J. L. Terán,
  • D. M. Aparicio

摘要

Abstract

In this work, we describe the synthesis of chiral (R)-(‒)-piperidine-2,4-dione derived from (R)-(‒)-phenylglycinol, a valuable building block for the diastereoselective synthesis of piperidine alkaloids. The key step involves intramolecular cyclization: when the electrophile is an ester, the reaction proceeds via the formation of a Grignard intermediate, whereas when the electrophile is a nitrile, the cyclization follows a Blaise-type mechanism.