Enantioselective Heck-Matsuda Reaction in non-Symmetric Cyclic Olefins: exploiting the catalyst control over the isomerization

• Grant number: 14/26055-9
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: April 01, 2015
• End date: August 31, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Francisco de Azambuja
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

Asymmetric catalysis is a permanent and highly relevant challenge in synthetic organic chemistry. Recently, the Heck arylation with aryldiazonium salts became part of a small group of asymmetric catalytic transformations employing chiral bidentate N,N-ligands. Nevertheless, this innovation is still a privilege for non-activated alkenes, cyclic or acyclic. Thus, it is our goal to develop this methodology further using cyclic non-symmetric olefins, aiming to control the C-C double bond migration. The desired Heck adducts constitutes concise approaches to densely functionalized building block in a stereoselective fashion. Preliminary results already demonstrated the viability of the proposed system, including good yields and moderate enantioselective in most cases.

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)

DE AZAMBUJA, FRANCISCO; CARMONA, RAFAELA C.; CHORRO, TOMAZ H. D.; HEERDT, GABRIEL; CORREIA, CARLOS ROQUE D.. Noncovalent Substrate-Directed Enantioselective Heck Reactions: Synthesis of S- and P-Stereogenic Heterocycles. CHEMISTRY-A EUROPEAN JOURNAL, v. 22, n. 32, p. 11205-11209, AUG 1 2016. (13/10183-5, 14/25770-6, 14/26055-9, 13/07600-3)