| Full text | |
| Author(s): |
Martins, Rodrigo S.
[1]
;
Zampieri, Davila S.
[1]
;
Rodrigues, J. Augusto R.
[1]
;
Carvalho, Patricia O.
[2]
;
Moran, Paulo J. S.
[1]
Total Authors: 5
|
| Affiliation: | [1] Univ Estadual Campinas, Inst Chem, BR-13084971 Campinas, SP - Brazil
[2] Univ Sao Francisco, BR-12916900 Braganca Paulista, SP - Brazil
Total Affiliations: 2
|
| Document type: | Journal article |
| Source: | CHEMCATCHEM; v. 3, n. 9, p. 1469-1473, SEP 2011. |
| Web of Science Citations: | 7 |
| 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. (AU) | |