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Regio and enantioselective Heck-Matsuda reaction with allylic alcohols using non symmetrical ligands

Grant number: 14/00588-0
Support Opportunities:Scholarships abroad - Research Internship - Doctorate
Effective date (Start): April 07, 2014
Effective date (End): March 29, 2015
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Carlos Roque Duarte Correia
Grantee:Caio Costa Oliveira
Supervisor: Andreas Pfaltz
Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
Research place: University of Basel, Switzerland  
Associated to the scholarship:11/01162-9 - A methodological and mechanistic study of the Heck-Matsuda reaction controlled by the substrate and synthetic applications., BP.DR


The first examples of the enantioselective Heck-Matsuda reaction were describedrecently by the group of Professor Correia. In spite of the good yields andenantiodiferentiation achieved for the desymmetrization of olefins using C2 symmetricbisoxazolines, the regioselective arylation of non-symmetrical substrates still remains adifficult task. To circumvent this problem we propose in this project the evaluation of thenonsymmetrical P,N ligands such phosphite-oxazolines and phophoramidite-oxazolineswhich have been developed in the group of Professor Pfaltz at the University of Basel. Themain objective of this project is to develop straightforward syntheses of enantioenriched aand beta aryl-aldehydes by the Pd-catalyzed arylation of allylic alcohols with aryldiazoniumsalts and its further application in the concise total syntheses of pharmacologically activecompounds. (AU)

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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)
OLIVEIRA, CAIO C.; PFALTZ, ANDREAS; DUARTE CORREIA, CARLOS ROQUE. Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 54, n. 47, p. 14036-14039, . (14/00588-0, 13/07600-3)

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