Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases

The oxidoreductases Lactobacillus brevis alcohol dehydrogenase (LBADH) and Candida parapsilosis carbonyl reductase (CPCR) are suitable catalysts for the reduction of ketones to afford enantiopure sec. alcohols. A broad variety of alkynones (1, 3, and 5) are accepted as substrates and the corresponding propargylic alcohols (2, 4, and 6) are obtained in good yield and excellent enantiomeric excess. By changing the steric demand of the substituents the ee values can be adjusted and even the configurations of the products can be altered