Enantioselective haloamination reactions aiming aminodiols synthesis

• Grant number: 16/17328-7
• Support Opportunities: Scholarships in Brazil - Master
• Effective date (Start): May 01, 2017
• Effective date (End): August 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Acordo de Cooperação: Coordination of Improvement of Higher Education Personnel (CAPES)
• Principal Investigator: Alessandro Rodrigues
• Grantee: Bruna Papa Spadafora
• 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 developing and studying 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). In the second stage of this proposal our goal involves the application of the products obtained by haloamination intramolecular reactions as intermediates in the synthesis of natural products Sphingosine and Jaspine's isomers, and evaluation of them 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. 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

(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)

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)