Linear free energy relationships in asymmetric catalysis

• Grant number: 22/14310-0
• Support Opportunities: Research Grants - Young Investigators Grants
• Start date: September 01, 2023
• End date: August 31, 2028
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Bruno Matos Paz
• Grantee: Bruno Matos Paz
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Associated scholarship(s): 24/20112-2 - Organocatalytic Enantioselective Synthesis of Rotenoids, BP.IC; 24/07892-9 - Computational and experimental study of catalytic enantioselective visible-light-mediated 6pi-photoelectrocyclization, BP.MS; 24/09518-7 - Linear Free Energy Relationships in Diels-Alder Aminocatalysed Reactions, BP.IC; 24/09649-4 - Linear Free Energy Relationships in Aminocatalyzed Michael Additions, BP.IC; 24/07893-5 - Asymmetric Organocatalysis in the Synthesis of New Artemisin Analogues, BP.DD

Abstract

In this proposal, studies that have asymmetric organocatalysis as a central theme will be coordinated. Starting from basic research (kinetic and methodology studies), tools will be developed aiming at future applications in translational research (medicinal chemistry and chemical biology). The project will start with the rational design of new organocatalysts and four privileged catalytic systems were selected as starting points: Jørgensen-Hayashi, Luo, MacMillan and Shi. The catalyst design will be guided by the current consensus on the elementary steps of the respective catalytic cycles. Successive localized structural modifications will be made in order to provide linear free energy relationships through kinetic studies. The trends observed at each iteration of catalysts aim to find organocatalysts that demonstrate catalytic efficiency (number and frequency of turnover) and stereoselectivity superior to the current state of the art in asymmetric organocatalysis. Once the proof of concept has been carried out, these catalytic systems will be applied in processes aiming to obtain enantioselectively compounds inspired by the structure of bioactive natural products: artemisinin, 8-tetrahydrocannabinoids and type A proanthocynidines. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

VIDAL-ALBALAT, ANDREU; MATOS PAZ, BRUNO. Organocatalytic Enantioselective Syntheses of Flavonoids and Cannabinoids. ADVANCED SYNTHESIS & CATALYSIS, v. 366, n. 5, p. 12-pg., 2023-11-28. (22/14310-0)