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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)

News published in Agência FAPESP Newsletter about the scholarship:
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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, . (16/00422-0)