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Arylation of Cycloalkenes via asymmetric Heck-Matsuda reaction and synthetic applications

Grant number: 13/10183-5
Support Opportunities:Scholarships in Brazil - Doctorate
Effective date (Start): September 01, 2013
Effective date (End): February 28, 2018
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Carlos Roque Duarte Correia
Grantee:Rafaela Costa Carmona
Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
Associated scholarship(s):16/00422-0 - Enantioselective construction of C-N bond by means of the Narasaka-Heck reaction, BE.EP.DR


The main objective of this study is the development of an asymmetric arylation methodology of cycloalkenes through the Heck-Matsuda reaction. The few examples available in the literature for this reaction have been developed in the laboratory of Professor Carlos Roque Duarte Correia at the Chemistry Institute of the State University of Campinas. Several types of olefins, such as indenes, dihydronaphthalenes and cyclopentenes will be employed in the asymmetric Heck-Matsuda reaction and the products obtained from these reactions will be employed in short synthetic routes for obtaining pharmacologically active compounds such as Indatraline, Irindalone, Sertraline, Tametraline and its derivatives. (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)
CARMONA, RAFAELA C.; KOSTER, OTTO D.; DUARTE CORREIA, CARLOS ROQUE. Chiral N,NLigands Enabling Palladium-Catalyzed Enantioselective Intramolecular Heck-Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 57, n. 37, p. 12067-12070, . (14/25770-6, 18/00271-8, 13/07600-3, 13/10183-5)
CARMONA, RAFAELA C.; CORREIA, CARLOS ROQUE D.. Stereoselective Synthesis of 3-Hydroxy-4-arylcyclopentanones and 4-Arylcyclopentenones through a Heck-Matsuda Desymmetrization of meso cis-4-Cyclopentene-1,3-diol. ADVANCED SYNTHESIS & CATALYSIS, v. 357, n. 12, p. 2639-2643, . (11/23832-6, 13/10183-5)
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, . (13/10183-5, 14/25770-6, 14/26055-9, 13/07600-3)
Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
CARMONA, Rafaela Costa. New applications of the enantioselective Heck reaction: desymmetrizations and intramolecular reactions. 2018. Doctoral Thesis - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.

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