Enantioselective bromoamination reactions aiming aminodiols synthesis

• Grant number: 16/13718-5
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: September 01, 2016
• End date: August 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Alessandro Rodrigues
• Grantee: Luiza Leticia Caccuri Rolim
• Host Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

This research proposal has as main topic an investigation on enantioselective bromoamination reactions promoted by organocatalysts, aiming the aminodiols synthesis, including the mechanistic aspects studies and the application of quiral synthetic intermediates in the synthesis of molecules with potential antitumor activity. The progress in the field of stereoselective catalysis is of utmost importance for the advancement of science of our country. The direct application of the proposed reactions intends to collaborate with the problems of scientific society in general, however, is a major challenge. In this project, simultaneously obtaining substituted conjugated allylic alcohols, selected organocatalysts derived from Cinchona alkaloids will be synthesised for the investigation in enantioselective bromoamination reactions. After the synthesis of bromoaminated alcohols, these will be submitted to aziridination/ring opening reaction sequences to the obtaintion of sphingosine, a long chain unsaturated aminodiol as well as structural analogs which will be tested against cancer cell lines.