Preparative-scale horse liver alcohol dehydrogenase catalyzed reductions of racemic cis and trans bicyclic 0-and S-heterocyclic ketones proceed with high enantiomeric selectivity. The diastereotopic selectivity for the pro-R faces of the carbonyl groups is also very high. The ee's of all but one of the product alcohols are >97%. The ee's of the recovered ketones are in the 5240% range. The results confirm that an ether-oxygen or -sulfur substituent does not alter the enzyme's overall structural specificity or stereospecificity toward i b ketone substrates.

No abstract