Baker's Yeast Mediated Reduction of Aromatic Ring Substituted 2-Tetralones

Article abstract of DOI:10.1016/0040-4020(95)00715-K

2-Tetralones mono- and disubstituted with methoxy or hydroxy groups in the aromatic ring are hydrogenated to 2-tetralols in good yields by non-fermenting baker's yeast.The prevalent enantioform of the reduction product and its e.e. were found to depend on the substitution pattern.In one case, i.e. the biotransformation of 5-methoxy-2-tetralone into the corresponding 2-tetralol, an e.e. >/= 98percent was observed.A simple abstract model for explaining and predicting the stereochemical outcome in the yeast-mediated carbonyl reduction of 2-tetralones is proposed.