Synthesis of the two enantiomers of 1-chloro-1,1-difluoro-3-(p-tolylsulphonyl)propan-2-ol by microbial reduction of the parent propanone and transformation into 3,3-difluorotetrahydrofuran derivatives

Abstract

Both R and S enantiomers of 1-chloro-1,1-difluoro-3-(p-tolylsulphonyl)propan-2-ol were obtained with high enantioselection by microbial reduction of 1-chloro-1,1-difluoro-3-(p-tolylsulphonyl)propan-2-one. The enantiomerically pure R-alcohol was obtained and transformed into 3,3-difluoro-4-methyl-2-[(p-tolylsulphonyl)methyl]tetrahydrofurans through a two-step synthesis.