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Asymmetric Counteranion-Directed Organocatalysis: Synthesis of Heterocyclic Systems and Peptides Functionalization

Grant number: 16/12622-4
Support Opportunities:Scholarships abroad - Research
Effective date (Start): October 20, 2016
Effective date (End): October 19, 2017
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Márcio Weber Paixão
Grantee:Márcio Weber Paixão
Host Investigator: F Dean Toste
Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
Research place: University of California, Berkeley (UC Berkeley), United States  

Abstract

This project aims to develop new protocols in asymmetric counteranion-directed catalysis - in this regard, the synthesis of heterocyclic scaffolds, unnatural amino acids and the late stage functionalization of peptides will be deeply investigated. Effectively, to achieve our goals, a chiral oxidative system, previously described by Toste Group (University of California at Berkeley), as well as, the cross-coupling dehydrogenative strategy will be employed. Furthermore, in collaboration with others groups, both computational and kinetic studies are going to be performed to the better understanding of catalytic properties.

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Scientific publications (4)
(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)
DA SILVA, VITOR A. F.; DA SILVA, GUSTAVO P.; MATSUO, BIANCA T.; ALI, AKBAR; DAVIS, REBECCA L.; ZUKERMAN-SCHPECTOR, JULIO; CORREA, ARLENE G.; PAIXAO, MARCIO W.. Synthesis of (Z)-beta-halo alpha,beta-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 17, n. 3, p. 519-526, . (16/12622-4, 15/17141-1, 14/50249-8, 16/14560-6)
ECHEMENDIA, RADELL; DA SILVA, GUSTAVO P.; KAWAMURA, MEIRE Y.; DE LA TORRE, ALEXANDER F.; CORREA, ARLENE G.; FERREIRA, MARCO A. B.; RIVERA, DANIEL G.; PAIXAO, MARCIO W.. A stereoselective sequential organocascade and multicomponent approach for the preparation of tetrahydropyridines and chimeric derivatives. CHEMICAL COMMUNICATIONS, v. 55, n. 3, p. 286-289, . (15/17141-1, 14/50249-8, 17/01754-0, 15/08541-6, 16/12622-4)
PADILLA, ROSA; JORGENSEN, MIKE S. B.; PAIXAO, MARCIO W.; NIELSEN, MARTIN. Efficient catalytic hydrogenation of alkyl levulinates to gamma-valerolactone. GREEN CHEMISTRY, v. 21, n. 19, p. 5195-5200, . (16/12622-4, 14/50249-8, 15/17141-1)
JORGE, ERLEN Y. C.; LIMA, CAROLINA G. S.; LIMA, THIAGO M.; MARCHINI, LUCAS; GAWANDE, MANOJ B.; TOMANEC, ONDREJ; VARMA, RAJENDER S.; PAIXAO, MARCIO W.. Sulfonated dendritic mesoporous silica nanospheres: a metal-free Lewis acid catalyst for the upgrading of carbohydrates. GREEN CHEMISTRY, v. 22, n. 5, p. 1754-1762, . (16/12622-4, 15/17141-1)

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