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Type: Artigo de periódico
Title: Stereoselective Oxidation of 1-Phenyl-1,2-propanediol Mediated by Microorganisms
Author: Martins, RS
Zampieri, DS
Rodrigues, JAR
Carvalho, PO
Moran, PJS
Abstract: The enantioselective oxidation of (1R,2S)-1-phenyl-1,2-propanediol [(1R,2S)-1], mediated by baker's yeast, gave (-)-(S)- 1-phenyl-2-hydroxy-1-propanone [(S)- 2] in 64% isolated yield and 93% ee. Kinetic experiments of the bio-oxidation of (+/-)-anti-1 revealed that the enantiomer (1R,2S)-1 was more reactive than (1S,2R)-1. Therefore, this result allowed us to devise a kinetic resolution experiment to obtain (1S,2R)-1 in > 99% ee from (+/-)-anti-1. The preparation of (1S,2R)-1 is interesting, as it is the antipode of the product obtained by the reduction of 1-phenyl-1,2-propanedione using baker's yeast. Other microorganisms, such as Micrococcus luteus, Candida albicans, and Geotrichum candidum, were also used for kinetic resolution experiments of (+/-)-anti-1. The best result was obtained using Geotrichum candidum, which gave (1S,2R)-1 in 32% yield and 99% ee.
Subject: alcohols
kinetic resolution
Country: EUA
Editor: Wiley-blackwell
Rights: fechado
Identifier DOI: 10.1002/cctc.201100145
Date Issue: 2011
Appears in Collections:Unicamp - Artigos e Outros Documentos

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