A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms

Abstract

Diastereoisomers (1 S,2 R,3 S)-, (1 R,2 R,3 S)-, (1 R,2 S,3 S)- and (1 S,2 S,3 S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1,3-butanedione, both involving in situ racemization. The first method comprised a one-pot microbial reduction coupled with a chemical reduction, while in the second method, stepwise chemo-enzymatic reductions were performed.