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Brönsted-Acid-Catalyzed Asymmetric Three-Component Reaction of Amines, Aldehydes, and Pyruvate Derivatives. Enantioselective Synthesis of Highly Functionalized γ-Lactam Derivatives

Author:
del Corte, Xabier, Maestro, Aitor, Vicario, Javier, Martinez de Marigorta, Edorta, Palacios, Francisco
Source:
Organic letters 2018 v.20 no.2 pp. 317-320
ISSN:
1523-7052
Subject:
Lewis bases, aldehydes, chemical reactions, diastereoselectivity, enamines, enantiomers, enantioselective synthesis, hydrogen bonding, imines, phosphoric acid, pyruvic acid
Abstract:
Chiral phosphoric acids are efficient organocatalysts for the asymmetric three-component reaction of amines, aldehydes, and pyruvate derivatives. Simultaneous condensation of amines with both carbonylic compounds followed by a hydrogen bonding activated nucleophilic addition of enamines to imines affords densely functionalized enantioenriched 1,5-dihydro-2H-pyrrol-2-ones. These substrates can be used in subsequent diastereoselective transformations to afford enantiopure γ-lactam derivatives.
Agid:
6083258