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Search for oxitants to enantioselective transformation of boron compounds

Grant number: 12/18960-8
Support type:Scholarships in Brazil - Doctorate
Effective date (Start): January 01, 2013
Effective date (End): March 31, 2016
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Leandro Helgueira de Andrade
Grantee:Rodrigo dos Santos Martins
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

The synthesis of chiral organoboranes is an interesting tool in organic synthesis, since boranes can be converted into different organic group such as alcohols, amines and organic halides with configuration retention.Organoboron oxidation by hydrogen peroxide is a common procedure for alcohol synthesis. The use of chiral organic hydroperoxide in the oxidation of organoboranes can be a useful strategy to obtain chiral alcohol and chiral boranes. Among the enantioselective organic oxidants with potential for enantioselective reactions, flavin hydroperoxides derivates, TADDOL hydroperoxide derivate and D-glucose-piruvate hydroperoxide derivate can be promissing.Biocatalysts can be also used in enantioselective oxidation of organoboranes, however there is few studies about the use of oxireductase enzymes in these oxidations. Among these enzymes we became interessed in monooxygenase flavin-dependent and monooxygenase heme-dependent which can catalyze heteroatom oxidation.In the present work we intend to investigate the oxidation of organoboron compounds by chiral organic hydroperoxides, heme-dependent monooxygenase and flavin-dependent monooxygenase. Then chemo- and enantioselectivity of these reactions, and factors that can influence this selectivity.