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Dynamic Kinetic Resolution study of primary amines catalyzed by nickel, aiming the synthesis of rasagiline analogs

Grant number: 18/13767-1
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): December 01, 2018
Effective date (End): November 30, 2019
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Fernanda Amaral de Siqueira
Grantee:Thayná Nunes de Carvalho Fernandes
Home Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

This project aims to study the dynamic kinetic resolution of primary amines with the use of nickel catalysts supported on mixed lanthanide oxides. The dynamic kinetic resolution (DKR) consists of a reaction in which an enzyme and a metal catalyst are used in order to produce enantiomerically pure molecules. These molecules are important in the manufacture of many drugs because of their biological activities. By means of this proposal will be evaluated the activity and selectivity of the metal catalyst in the racemization stage of DKR. We will also study the variation of other conditions of the reaction medium, such as temperature and time, in order to provide better results for obtaining the corresponding chiral acetamide. In addition, DKR will be used as a key step in the synthesis of N-propargyl substituted compounds, employing as DKR later steps alkylation of (R) -1-phenylethylacetamide, followed by hydrolysis of the acetate group, in order to obtain analogues of rasagiline, which consists of a drug used in the treatment of Parkinson's Disease.