Tetrahedron Letters p. 6089 - 6092 (1985)
Update date:2022-08-11
Topics:
Fujisawa, Tamotsu
Kojima, Eiji
Itoh, Toshiyuki
Sato, Toshio
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.
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