Artículos de revistas
Stereoselective Oxidation of 1-Phenyl-1,2-propanediol Mediated by Microorganisms
Registro en:
Chemcatchem. Wiley-blackwell, v. 3, n. 9, n. 1469, n. 1473, 2011.
1867-3880
WOS:000295228400015
10.1002/cctc.201100145
Autor
Martins, RS
Zampieri, DS
Rodrigues, JAR
Carvalho, PO
Moran, PJS
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) 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. 3 9 1469 1473 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) FAPESP [03/05882-0]