Organocatalysis: design, synthesis and applications in stereoselective organic reactions

• Grant number: 13/10073-5
• Support Opportunities: Regular Research Grants
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Alessandro Rodrigues
• Grantee: Alessandro Rodrigues
• Host Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

This proposal focuses on the use of computational methods for the development of organic catalysts along with their applications in synthetically useful stereoselective reactions. The rational design of new chiral catalysts has been a challenge to chemistry. Thus, molecular modeling applied to stereoselective catalysis will have crucial role in this project, aimed at developing new technologies that address the current and future needs of the chemistry and the society in general.The asymmetric organocatalysis is an area that has vast potential for the synthesis of synthetic intermediates with high added value. We intend to cooperate with this expanding area of research, investigating the synthesis and application of novel catalysts and substrates in reactions rarely or never explored in organocatalysis. We seek to develop new chiral organocatalysts based on thiourea functional group, applying them in various stereoselective reactions of interest, such as: Henry reaction (nitroaldol), Michael reaction, Friedel-Crafts/Michael reaction and Michael/Henry reaction.During the progress of the study, we intend to introduce and consolidate a new line of research in the field of asymmetric catalysis guided by theoretical calculations at UNIFESP-Diadema. We also intend to train human resources in this field. (AU)

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)

RODRIGUES, ALESSANDRO; OLIVATO, PAULO R.; ZUKERMAN-SCHPECTOR, JULIO; MAGANHI, STELLA H.; REIS, ADRIANA K. C. A.; TIEKINK, EDWARD R. T.. Molecular Structures of Isomeric Ortho, Meta, and Para Bromo-Substituted alpha-Methylsulfonyl-alpha-diethoxyphosphoryl Acetophenones by X-ray and DFT Molecular Orbital Calculations. Journal of Physical Chemistry A, v. 119, n. 32, p. 8714-8723, AUG 13 2015. (13/16644-4, 13/10073-5)

LEVY, DEBORA; DE MELO, THATIANA CORREA; OHIRA, BIANCA YUMI; FIDELIS, MAIRA LUISA; RUIZ, JORGE L. M.; RODRIGUES, ALESSANDRO; BYDLOWSKI, SERGIO P.. Oxysterols selectively promote short-term apoptosis in tumor cell lines. Biochemical and Biophysical Research Communications, v. 505, n. 4, p. 1043-1049, NOV 10 2018. (16/21676-0, 13/10073-5)

PAZ, JESSICA LILIANE; LEVY, DEBORA; OLIVEIRA, BEATRIZ ARAUJO; DE MELO, THATIANA CORREIA; DE FREITAS, FABIO ALESSANDRO; REICHERT, CADIELE OLIANA; RODRIGUES, ALESSANDRO; PEREIRA, JULIANA; BYDLOWSKI, SERGIO PAULO. 7-Ketocholesterol Promotes Oxiapoptophagy in Bone Marrow Mesenchymal Stem Cell from Patients with Acute Myeloid Leukemia. CELLS, v. 8, n. 5, MAY 2019. (16/21676-0, 13/10073-5)

LEVY, DEBORA; DE MELO, THATIANA CORREA; OLIVEIRA, BEATRIZ A.; PAZ, JESSICA L.; DE FREITAS, FABIO A.; REICHERT, CADIELE O.; RODRIGUES, ALESSANDRO; BYDLOWSKI, SERGIO P.. 7-Ketocholesterol and cholestane-triol increase expression of SMO and LXR alpha signaling pathways in a human breast cancer cell line. BIOCHEMISTRY AND BIOPHYSICS REPORTS, v. 19, p. 6-pg., 2019-09-01. (13/10073-5, 16/21676-0)