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 Opportunities: Scholarships in Brazil - Doctorate (Direct)
• Start date: August 01, 2015
• End date: January 12, 2021
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Fernando Antonio Santos Coelho
• Grantee: Hugo dos Santos
• Host 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)

Scientific publications

(11)

(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)

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. (13/07600-3, 15/09205-0, 18/02611-0, 17/02364-0)

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. (15/09205-0, 13/10449-5, 13/07600-3)

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. (15/09205-0, 18/02611-0, 13/07600-3, 16/23005-6)

SENNA, ANA JULIA S.; RODRIGUES JR, MANOEL T.; SANTOS, HUGO; ZEOLY, LUCAS A.; GOMES, RALPH C.; COELHO, FERNANDO. 1,6-Addition of indolizines to para-quinone methides with indium(III) chloride as catalyst. Tetrahedron Letters, v. 125, p. 6-pg., 2023-07-05. (13/07600-3, 18/02611-0, 15/09205-0)

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. (18/02611-0, 13/07600-3, 16/23005-6, 15/09205-0)

CAMILO, NILTON S.; SANTOS, HUGO; ZEOLY, LUCAS A.; FERNANDES, FABIO S.; RODRIGUES JR, MANOEL T.; SILVA, THIAGO S.; LIMA, SAMIA R.; SERAFIM, JOSE CLAUDIO; DE OLIVEIRA, ALINE S. B.; CARPANEZ, ARTHUR G.; et al. An Improved Protocol for the Morita-Baylis-Hillman Reaction Allows Unprecedented Broad Synthetic Scope. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. N/A, p. 9-pg., 2022-01-19. (18/00299-0, 18/02611-0, 16/23005-6, 13/07600-3, 15/09205-0)

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, v. N/A, p. 60-pg., 2020-01-01. (17/02364-0, 13/07600-3, 18/02611-0, 15/09205-0)

SANTOS, HUGO; ZEOLY, LUCAS A.; RODRIGUES JR, MANOEL T.; FERNANDES, FABIO S.; GOMES, RALPH C.; ALMEIDA, WANDA P.; COELHO, FERNANDO. Recent Advances in Catalytic Systems for the Mechanistically Complex Morita-Baylis-Hillman Reaction. ACS CATALYSIS, v. 13, n. 6, p. 32-pg., 2023-03-17. (13/07600-3, 15/09205-0)

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. (15/09205-0, 13/10449-5, 13/07600-3)

ZEOLY, LUCAS A.; ACCONCIA, LAIS V.; RODRIGUES JR, MANOEL T.; SANTOS, HUGO; CORMANICH, RODRIGO A.; PANIAGUA, JUAN C.; MOYANO, ALBERT; COELHO, FERNANDO. One-pot organocatalyzed synthesis of tricyclic indolizines. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 21, n. 17, p. 15-pg., 2023-04-14. (13/07600-3, 14/26027-5, 13/24386-5, 18/02611-0, 15/00975-7, 15/09205-0)

CORMANICH, RODRIGO A.; ZEOLY, LUCAS A.; SANTOS, HUGO; CAMILO, NILTON S.; BUHL, MICHAEL; COELHO, FERNANDO. Origin of the Diastereoselectivity of the Heterogeneous Hydrogenation of a Substituted Indolizine. Journal of Organic Chemistry, v. 85, n. 17, p. 8-pg., 2020-09-04. (13/07600-3, 18/03910-1, 15/09205-0)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

SANTOS, Hugo dos. Development of new catalytic methodologies for the synthesis of heterocyclic compounds. 2023. Doctoral Thesis - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.