Diastereo-and enantioselective reduction of α, β-diketodithiane with the baker's yeast

T Fujisawa, E Kojima, T Itoh, T Sato

Index: Fujisawa, Tamotsu; Kojima, Eiji; Itoh, Toshiyuki; Sato, Toshio Tetrahedron Letters, 1985 , vol. 26, # 49 p. 6089 - 6092

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Citation Number: 38

Abstract

Abstract 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, 23-(+)-(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 ...