Combining Organo- and Biocatalysis

Significance

The authors report a chemoenzymatic reaction sequence towards 1,3-diols. The reported route consists of the amine-1-catalyzed aldol addition of acetone to aromatic aldehydes with a subsequent alcohol dehydrogenase (ADH) catalyzed ketoreduction. The co-factor NADH or NADPH, depending on the involved enzyme, respectively, was used in only catalytic amounts, enabled by a substrate-coupled regeneration process. The stereochemical outcome of the reaction could be fully controlled. With the four possible combinations of (S,S)-1, (R,R)-1 and (S)-ADH, (R)-ADH all diastereoisomers of each product could be obtained with excellent diastereo- and enantiocontrol.