Enantioselective construction of C-N bond by means of the Narasaka-Heck reaction

• Grant number: 16/00422-0
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• Start date: May 01, 2016
• End date: April 30, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Rafaela Costa Carmona
• Supervisor: John Bower
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Institution abroad: University of Bristol, England
• Associated to the scholarship: 13/10183-5 - Arylation of Cycloalkenes via asymmetric Heck-Matsuda reaction and synthetic applications, BP.DR

Abstract

New methods for the formation of nitrogen substituted stereocentresare of great interest due to their applicability to the synthesisof pharmaceutically active compounds. An efficient example includes the Narasaka-Heck cyclization. The first enantioselective examples of this reaction were recently described by Bowerand co-workers. Despite the good yields and enantioselectivityachieved the reaction is somewhat limited by the use of trisubstituted olefins in order to avoid aromatization of the end product.In this project, we propose to overcome this problem by the evaluation of redox relay processesthat use directing groups to enable control of double bond migration along a carbon chain. Accordingly, the main objective of this project is to develop a straightforward and regiocontrolled methodologyto access diverse enantioenrichedN-heterocyclic scaffolds by the Narasaka-Heck reaction. (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)

HAZELDEN, IAN R.; CARMONA, RAFAELA C.; LANGER, THOMAS; PRINGLE, PAUL G.; BOWER, JOHN F.. Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 57, n. 18, p. 5124-5128, APR 23 2018. (16/00422-0)