Pig liver alcohol dehydrogenase catalysed stereoselective reduction of cage-shaped ketones. Preparation of axially chiral (–)-(R)-adamantane-2,6-diol with high enantiomeric purity

Abstract

In a study of the stereoselective reductions of various cage-shaped ketones catalysed by pig liver alcohol dehydrogenase (PLADH), a typical axially chiral diol, (–)-(R)-adamantane-2,6-diol 12a with high enantiomeric purity was prepared by asymmetric reduction of keto ester 11d; based on this a new, remarkable function of the active site of the enzyme, which serves to enhance the stereoselectivity of the reaction is suggested.