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New frontiers of the Morita-Baylis-Hillman reaction: 1) New applications of a bifunctional catalyst derived from imidazole. 2) Studies on the asymmetric synthesis of a natural high-potency sweetener

Grant number: 15/09205-0
Support type:Scholarships in Brazil - Doctorate (Direct)
Effective date (Start): August 01, 2015
Effective date (End): January 12, 2021
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Fernando Antonio Santos Coelho
Grantee:Hugo dos Santos
Home Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

This PhD project aims to explore the potentiality of the Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of commercially important biologically active substances. The project is divided in two subprojects. In the first one, we intend to increase the scope for the use of a bifunctional base, recently used in our research group, as catalyst for the Morita-Baylis-Hilman reaction. We are interested in using unsaturated lactams, lactones and cyclic ketones for these reactions. We also intend to study the development of an asymmetric version for this reaction. In the second subproject, we will revisit the synthesis of a molecule from natural source, which presents a high activity as sweetener. A new proposal for the synthesis of Monatin will be the target of this subproject. We intend to use a Morita-Baylis-Hillman adduct as substrate for this asymmetric total synthesis. (AU)

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Scientific publications (5)
(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)
FERNANDES, FABIO S.; SANTOS, HUGO; LIMA, SAMIA R.; CONTI, CAROLINE; RODRIGUES JR, MANOEL T.; ZEOLY, LUCAS A.; FERREIRA, LEONARDO L. G.; KROGH, RENATA; ANDRICOPULO, ADRIANO D.; COELHO, FERNANDO. Discovery of highly potent and selective antiparasitic new oxadiazole and hydroxy-oxindole small molecule hybrids. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v. 201, SEP 1 2020. Web of Science Citations: 0.
RODRIGUES JR, MANOEL T.; SANTOS, HUGO; ZEOLY, LUCAS A.; SIMONI, DEBORAH A.; MOYANO, ALBERT; COELHO, FERNANDO. Preparation of tetrahydro-1H-xanthen-1-one and chromen-1-one derivatives via a Morita-Baylis-Hillman/oxa-Michael/elimination cascade. ARKIVOC, n. 2, p. 77+, 2020. Web of Science Citations: 0.
SILVA, THIAGO S.; RODRIGUES, JR., MANOEL T.; SANTOS, HUGO; ZEOLY, LUCAS A.; ALMEIDA, WANDA P.; BARCELOS, ROSIMEIRE C.; GOMES, RALPH C.; FERNANDES, FABIO S.; COELHO, FERNANDO. Recent advances in indoline synthesis. Tetrahedron, v. 75, n. 14, p. 2063-2097, APR 5 2019. Web of Science Citations: 6.
RAICH, LLUIS; SANTOS, HUGO; GOMES, JULIANA C.; RODRIGUES, JR., MANOEL T.; GALAVERNA, RENAN; EBERLIN, MARCOS N.; COELHO, FERNANDO; ROVIRA, CARME; MOYANO, ALBERT. Can an Alcohol Act As an Acid/Base Catalyst in Water Solution? An Experimental and Theoretical Study of Imidazole Catalysis of the Aqueous Morita-Baylis--Hillman Reaction. ACS CATALYSIS, v. 8, n. 3, p. 1703-1714, MAR 2018. Web of Science Citations: 5.
GOMES, RALPH C.; BARCELOS, ROSIMEIRE C.; RODRIGUES, JR., MANOEL T.; SANTOS, HUGO; COELHO, FERNANDO. Intermolecular Stetter Reactions on Morita-Baylis-Hillman Adducts: an Approach to Highly Functionalized 1,4-Dicarbonyl Compounds. CHEMISTRYSELECT, v. 2, n. 3, p. 926-930, JAN 2017. Web of Science Citations: 1.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.