One-pot synthesis of γ-lactams from ketoaziridines

Author(s)

Martelli, Lorena S. R. ; da Silva, Otavio A. M. ; Zukerman-Schpector, Julio ; Correa, Arlene G.

• Document type: Journal article
• Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 21, n. 46, p. 5-pg., 2023-11-09.

Abstract

The remarkable biological activities of gamma-lactams have stimulated the search for efficient synthetic methods to achieve these scaffolds. In this work, we have developed a simple one-pot diastereoselective synthesis of new gamma-lactams from ketoaziridines with moderate to good yields via the Horner-Wadsworth-Emmons reaction, followed by an intramolecular ester-aziridine cyclization and its opening in situ. Preliminary efforts towards an enantioselective version of this method are also reported. New gamma-lactams were obtained in a one-pot procedure from ketoaziridines in moderate to good overall yields. (AU)

• FAPESP's process: 18/23761-0 - Stereoselective synthesis of heterocycles from the opening of chiral epoxides or azidirines
• Grantee: Lorena Suelen Ribeiro Martelli
• Support Opportunities: Scholarships in Brazil - Doctorate
• 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: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 14/50918-7 - INCT 2014: for the Biorational Control of Pest-Insect and Phytopathogens
• Grantee: Maria Fátima das Graças Fernandes da Silva
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program