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Study of dynamic kinetic resolution of substituted and cyclic primary amines with palladium catalyst supported on dolomite.

Grant number: 22/10802-6
Support Opportunities:Scholarships in Brazil - Scientific Initiation
Effective date (Start): December 01, 2022
Effective date (End): May 31, 2024
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Fernanda Amaral de Siqueira
Grantee:Larissa Moises da Silva
Host Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

his project aims to study the dynamic kinetic resolution (DKR) of primary amines in which a palladium catalyst supported on dolomite will be used. DKR consists of a reaction in which an enzyme and a metallic catalyst are used in order to produce enantiomerically pure molecules from a racemic mixture. Chiral amines are important building blocks for the synthesis of many drugs. In this proposal, the reactivities of 1 substituted primary amine and 3 that present a cyclic system in their structure will be evaluated, in order to generalize the studies that were initiated in our research group.Initially, the DKR reactions will be carried out under the same conditions used for the model compound (1-phenylethiamine). These reaction conditions will be adjusted to better meet the reactivity of the compounds of the present proposal, starting with the use of toluene as a solvent and then with the use of ionic liquids as additives or solvents. We will seek the best reaction conditions to obtain the corresponding acetamide in satisfactory conversions and enantiomeric excesses, which will involve not only the search for an alternative solvent, but also an acylating agent, temperature and reaction time that provide us with the best possible results.

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