Sintese enantiosseletiva de efedrina

AUTOR(ES)

Emerson Lourenço

DATA DE PUBLICAÇÃO

2003

RESUMO

In this work, some methodologies for enantioselective reduction of the prochiral diketone 1-phenyl-1,2-propanedione (3) mediated by Baker´s Yeast (Saccharomyces cerevisiae) had been studied. This diketone was synthesized by a-oxymation of propiophenone (7) (68-80%), followed by acidic hydrolysis of (2E)-1-phenyl-1,2-propanodione 2-oxime (8) (62-77%). The great interest on microbial reduction of 3 is to access (R)-1-hydroxy-1-phenyl-2-propanone (4), because (R)-4 can undergo a reductive amination producing aminoalcohols in high e.e. Thus, (R)-4 was obtained, 21% of isolated yield and 96% e.e., using a nitrogen/oxygen bubbling reduction condition of 3. Other two compounds were obtained from 3, under different conditions; (S)-2-hydroxy-1-phenyl-1-propanone (5) (45-68%; 96% e.e.) and (1R,2S)-1-phenyl-1,2-propanediol (6) (74-97%; >99% e.e.). Some routes were developed in order to obtain chiral aminoalcohols from these compounds.

ASSUNTO(S)

biotransformação (metabolismo) hidrolise saccharomyces cerevisiae

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