Diastereoselective Synthesis of Highly Functionalized γ-Lactams via Ugi Reaction/Michael Addition

The γ-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the γ-lactams, 2-oxopyrrolidine-3-carbonitrile derivatives stand out as versatile synthons that can be readily transformed into a variety of othe...

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Bibliographic Details
Published in:	Chemistry, an Asian journal p. e202400917
Main Authors:	Correa, Arlene, Vidal, Herika Danielle Almeida, Januario, Marcelo Augusto Pereira, Martinez, Alice Karoline de Almeida, Nunes, Paulo Sergio Gonçalves, Santiago, Pedro Henrique de Oliveira, Ellena, Javier Alcides
Format:	Journal Article
Language:	English
Published:	Germany 09-11-2024
Subjects:	Michael addition 3-cyano-2-pyrrolidinones one-pot reactions γ-lactams Ugi reaction
Online Access:	Get full text
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Summary:	The γ-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the γ-lactams, 2-oxopyrrolidine-3-carbonitrile derivatives stand out as versatile synthons that can be readily transformed into a variety of other functional groups. In this work, we successfully synthesized highly functionalized 3-cyano-2-pyrrolidinones with moderate to good overall yields using the Ugi reaction followed by intramolecular Michael addition. The process demonstrated excellent diastereoselectivity and showed good tolerance to a range of isonitriles and carbonyl compounds.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1861-4728 1861-471X 1861-471X
DOI:	10.1002/asia.202400917