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

Francisco Palacios presents an asymmetric three-component reaction of amines, aldehydes and pyruvate derivatives.

At the heart of diversity-oriented synthesis, multicomponent reactions (MCRs) are valuable synthetic protocols where three or more components react together in a single vessel to afford densely functionalized substrates, where a substantial part of the structure of all the starting materials can be found in the final substrate. Hantzsch dihydropyridine synthesis, Biginelli, Ugi, Passerini, Gröbcke–Blackburn–Bienaymé, Kabachnik–Fields or Strecker reactions are notorious examples of extremely useful MCR protocols. As a contribution to this field, the research group of Professor Francisco Palacios (University of the Basque Country, Vitoria-Gasteiz, Spain) reported a few years ago an acid-catalyzed three component reaction of amines, aldehydes and ethyl pyruvate to afford 3-amino-1,5-dihydro-1H-pyrrol-2-ones. Considering the fast development of organocatalysis during recent decades and particularly the Brønsted acid catalyst, the group was intrigued whether the stereocontrolled formation of the C–C bond in their three-component reaction could be achieved if chiral phosphoric acids were used as catalytic species.


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