Synthesis of pharmacologically active compounds by the enantioselective Heck-Matsuda reaction and novel studies concerning the enantioselective acylation of cyclopentenes and cyclohexene compounds

• Grant number: 17/21494-2
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: March 01, 2018
• End date: February 28, 2021
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Martí Fernández Wang
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated research grant: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes, AP.TEM

Abstract

The present proposal is divided into two projects. The first one involves the synthetic application of the enantioselective Heck-Matsuda reaction. More precisely, the application of the key product of the desymmetrization of achiral cyclopent-3-enol in total syntheses of pharmacologically active compounds, such as (+)-indatraline (+)-irindalone and prostaglandin analogues. The second project aims at expanding the type of olefins used in the enantioselective Heck reactions. To this goal in mind, we are proposing the investigation of the enantioselective Heck-Matsuda and oxidative Heck reactions using olefins such as cyclopentene and cyclohexene as substrates aiming at adding synthetic value to these compounds. The reaction conditions will be optimized in order to obtain key arylated products in high yields and enantioselectivities. (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)

POLO, ELLEN CHRISTINE; WANG, MARTI FERNANDEZ; ANGNES, RICARDO ALMIR; BRAGA, ATAUALPA A. C.; DUARTE CORREIA, CARLOS ROQUE. Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity. ADVANCED SYNTHESIS & CATALYSIS, v. 362, n. 4, DEC 2019. (19/02052-4, 14/25770-6, 13/07600-3, 15/01491-3, 17/21494-2)