DIASTEREO- AND ENANTIOSELECTIVE REDUCTION OF α,β-DIKETODITHIANE WITH THE BAKER'S YEAST

Article abstract of DOI:10.1016/S0040-4039(00)95133-5

The Baker's yeast reduction of 1-(1,3-dithian-2-yl)-1,2-propanedione gave highly enantio- and diastereoselectively (S)-(+)-1-(1,3-dithian-2-yl)-2-hydroxy-1-propanone or (1S,2S)-(+)-1-(1,3-dithian-2-yl)-1,2-propanediol, depending on the reaction time.The hydroxy ketone was reduced with diisobutylaluminum hydride to give (1R,2S)-1-(1,3-dithian-2-yl)-1,2-propanediol with high diastereoselectivity.The former (1S,2S)-diol was converted into L-digitoxose.