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

Author(s)

Vidal, Herika D. A. ; Nunes, Paulo S. G. ; Martinez, Alice K. A. ; Januario, Marcelo A. P. ; Santiago, Pedro H. O. ; Ellena, Javier ; Correa, Arlene G.

• Document type: Journal article
• Source: CHEMISTRY-AN ASIAN JOURNAL; v. N/A, p. 7-pg., 2024-11-09.

Abstract

The gamma-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the gamma-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. (AU)

• FAPESP's process: 19/06555-0 - Michael addition organocatalyzed and multicomponent one-pot reactions
• Grantee: Paulo Sérgio Gonçalves Nunes
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 17/15850-0 - X-ray diffraction as a tool in potential drug development
• Grantee: Eduardo Ernesto Castellano
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 24/05518-2 - Synthesis of five-membered N-heterocycles employing green methods
• Grantee: Alice Karoline de Almeida Martinez
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 21/12394-0 - Sustainable synthetic methods employing catalysis, benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 21/10066-5 - Crystallographic and structural study of new substances with potential biological activities
• Grantee: Pedro Henrique de Oliveira Santiago
• Support Opportunities: Scholarships in Brazil - Post-Doctoral