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Evaluation of lipases, transaminases and enoato reductases as catalysts in synthesis of chiral organoboron compounds.

Grant number: 09/17919-1
Support type:Scholarships in Brazil - Doctorate
Effective date (Start): March 01, 2010
Effective date (End): September 30, 2013
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Leandro Helgueira de Andrade
Grantee:Joel Savi dos Reis
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

Our work will be focused on the application of enoate reductases in the synthesis of chiral organoboron compounds, by an enantioselective reduction of vinyl organoboranes. After that, our efforts will be dedicated to the application of lipases as catalysts in the resolution of aminoboronic compounds. The kinetic resolution will be performed by an enantioselective acylation. Furthermore, we'll evaluate the dynamic kinetic resolution, which use a lipase as resolution agent, and metals, such as palladium or ruthenium as racemization agent. Besides, we intend to employ of transaminases as resolution catalysts. At this last stage, the kinetic resolution of aminoboronic substrates will be carry out by enantioselective oxidation catalyzed by transaminases. The transaminases also will be also employed as catalysts of reductive amination of ketones containing a boronic group.