Stereoselective Oxidation of 1-Phenyl-1,2-propanediol Mediated by Microorganisms

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.3914691473Fundação 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