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Study of Heck arylation reaction of non-activated olefins with diazonium salts and their application in stereo controlled total synthesis of neuro excitatory amino acids of the acromelate family

Grant number: 05/05150-4
Support Opportunities:Scholarships in Brazil - Doctorate
Effective date (Start): April 01, 2006
Effective date (End): February 28, 2010
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Carlos Roque Duarte Correia
Grantee:Angélica Venturini Moro
Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil


The research proposal deals with a detail study of the Heck arylation reaction catalyzed by zerovalent palladium envolving arenediazonium tetrafluoroborates of chiral non-activated olefins of the type 3,4-dehydroprolines. Complementing previous recent studies, several other arenediazonium salts will be tested, including ones bearing electron-withdrawing groups of various types, polyhidroxylated arenediazonium salts and arenediazonium salts derived from pyridine in its free or N-oxide form. The influence of the substitution pattern will also be investigated aiming at future applications of the methodology. The 4-aryl-2,3-dehydroprolines, the final Heck adducts, will be employed in the total stereocontrolled synthesis of the acromelic acids. These compounds are highly neuroexcitatory compounds and of great relevance for farmacological and medicinal studies.

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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)
MORO, ANGELICA VENTURINI; PEREIRA CARDOSO, FLAVIO SEGA; DUARTE CORREIA, CARLOS ROQUE. Highly Regio- and Stereoselective Heck Reaction of Allylic Esters with Arenediazonium Salts: Application to the Synthesis of Kavalactones. ORGANIC LETTERS, v. 11, n. 16, p. 3642-3645, . (05/05150-4)
Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
MORO, Angélica Venturini. Heck arylations with diazonium salts: methodology and applications in the synthesis of chiral ligands, natural products and analogues. 2010. Doctoral Thesis - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.

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