Intramolecular Cyclization of Grignard or Blaise Intermediates for the Synthesis of a Chiral Piperidine-2,4-dione Derived from (R)-(‒)-Phenylglycinol
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.
Authors
- David M. Aparicio (ORCID: https://orcid.org/0000-0003-3112-5335)
- Vladimir Carranza (ORCID: https://orcid.org/0000-0003-0427-4298)
- Angel Palillero‐Cisneros (ORCID: https://orcid.org/0000-0002-1008-1532)
- Joel L. Terán (ORCID: https://orcid.org/0000-0002-4055-4353)
- Jorge R. Juárez (ORCID: https://orcid.org/0000-0002-2553-5285)
- Alan Carrasco‐Carballo (ORCID: https://orcid.org/0000-0003-1065-4211)
- Angélica Aguilar‐Aguilar (ORCID: https://orcid.org/0000-0001-5924-6986)
- Hisami Rodríguez‐Matsui (ORCID: https://orcid.org/0000-0003-0817-1499)
Institutions
- Laboratoire de Synthèse Organique (FR)
- Chemical Synthesis Lab (SG)
- Benemérita Universidad Autónoma de Puebla (MX)
Publication Details
- Journal
- Russian Journal of Organic Chemistry
- Published
- 2025-05-01
- DOI
- https://doi.org/10.1134/s1234567824604194
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00