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