Synthesis of N-heterocycles via asymmetric Ugi-type multicomponent reactions

• Grant number: 23/13505-5
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: November 01, 2023
• End date: October 31, 2025
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: Thiago Sabino da Silva
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated research grant: 21/12394-0 - Sustainable synthetic methods employing catalysis, benign solvents, safer reagents, and bio-renewable feedstock, AP.TEM

Abstract

In modern organic chemistry, there's a pressing need to design new synthetic methods that can rapidly craft intricate molecules from simple starting materials, emphasizing both diversity and function-oriented synthesis. Multicomponent reactions (MCRs) are a highly effective approach for efficiently generating structural diversity and molecular complexity. Among various MCRs, isocyanide-based multicomponent reactions (IMCRs) are particularly remarkable for their capacity to yield highly functionalized molecules with outstanding chemical efficiency, convergence, and atom economy. With this goal in mind, we envisioned the development of an asymmetric Ugi-type reaction employing both chiral and achiral hemiacetals, utilizing an organocatalytic Brønsted acid as the source of asymmetric induction. Furthermore, the resulting compounds may serve as valuable chemical biology tools with potential for biological property evaluation.