Enantioselective haloamination reactions aiming the synthesis of aminodiols

• Grant number: 16/21676-0
• Support Opportunities: Regular Research Grants
• Duration: February 01, 2017 - February 28, 2019
• 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
• Associated researchers: Débora Levy ; Diogo de Oliveira Silva ; Elisângela Vinhato ; Sergio Paulo Bydlowski ; Thiago Carita Correra

Abstract

This proposal focuses on studying and development of enantioselective haloamination reactions aiming the aminodiols synthesis. The allyl alcohol and especially its structural analogues are organic compounds of great interest to the academic community, as they allow a range of chemical transformations. In the first stage of this proposal we intend to develop a pioneer enantioselective version of intramolecular haloamination reactions on readily available allylic alcohols promoted by palladium(II)/copper(II) and organocatalysts. Adicionally, the products obtained by haloamination intramolecular reactions will be used as intermediates in the synthesis of natural products Sphingosine and Jaspine's isomers. The Sphingosine and Jaspines will be evaluated as antitumor agents against cell lines of breast cancer (MDA-MB 231), small cell lung cancer (A549) and murine melanoma (B16-F12). Alongside the catalytic studies, an investigation by mass spectrometry and theoretical calculations will be performed aiming to propose a catalytic-cycle for the haloamination reaction (by metal and organic catalysis), and the reactive intermediates will be identifying through analytic techniques. It is intended by the proposition of the catalytic-cycle, understanding the root cause of possible regio-, diastereo- and enantioselectivity. With the development of this proposal is expected to cooperate with the increase and diversification of scientific and technological productivity of Brazilian research in addition to expanding the knowledge of organic chemistry that may be useful to the scientific community. (AU)

Scientific publications

(6)

(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)

VALENCA, J.; OLIVATO, PAULO R.; RODRIGUES, DANIEL N. S.; BATISTA, PATRICK R.; DUCATI, LUCAS C.; DAL COLLE, MAURIZIO. Conformational analysis and electronic interactions of some 2-[2 `-(4 `-sustituted-phenylsulfanyl)-acetyl]-5-substituted furans and 2-[2 `-(phenylselanyl)-acetyl]-5-methylfuran. Journal of Molecular Structure, v. 1225, FEB 5 2021. (17/17750-3, 16/21676-0, 18/07308-4)

VALENCA, J.; OLIVATO, PAULO R.; RODRIGUES, DANIEL N. S.; TRAESEL, HENRIQUE J.; ZUKERMAN-SCHPECTOR, JULIO; DAL COLLE, MAURIZIO. Conformational analysis and electronic interactions of some 2-[2 `-(4 `-substituted-phenylsulfinyl)-acetyl]-5-methylfurans. Journal of Molecular Structure, v. 1196, p. 793-804, NOV 15 2019. (16/21676-0)

TRAESEL, HENRIQUE J.; OLIVATO, PAULO R.; RODRIGUES, DANIEL N. S.; VALENCA, JESSICA; RODRIGUES, ALESSANDRO; ZUKERMAN-SCHPECTOR, JULIO; DAL COLLE, MAURIZIO. Spectroscopic and theoretical studies of some 2-(methoxy)-2-[(4-substituted)-phenylsulfany1]-(4 `-substituted) acetophenones. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, v. 210, p. 82-97, MAR 5 2019. (16/21676-0)

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; 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)

PAPA SPADAFORA, BRUNA; MOREIRA RIBEIRO, FRANCISCO WANDERSON; MATSUSHIMA, JULLYANE EMI; ARIGA, ELAINE MIHO; OMARI, ISAAC; SOARES, PRISCILA MACHADO ARRUDA; DE OLIVEIRA-SILVA, DIOGO; VINHATO, ELISANGELA; MCINDOE, J. SCOTT; CARITA CORRERA, THIAGO; et al. Regio- and diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 19, n. 25, JUN 2021. (19/16026-5, 16/21676-0, 15/08539-1, 16/17328-7, 17/18485-1, 14/15962-5, 19/25634-9)