Asymmetric syntheses via enantiotopically selective horse liver alcohol dehydrogenase catalyzed oxidations of diols containing a prochiral center

AJ Irwin, JB Jones

Index: Irwin,A.J.; Jones,J.B. Journal of the American Chemical Society, 1977 , vol. 99, p. 556 - 561

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Citation Number: 94

Abstract

Abstract: The practicality of exploiting the enantiotopic specificity of horse liver alcohol dehydrogenase (HLADH) has been demonstrated using substituted pentane-l, 5-diol substrates in which C-3 is a prochiral center. The catalysis was stereoselective for the pro 3 hydroxyl group in each case. HLADH catalyzed oxidation of 3-methylpentane-l, 5-diol gave (3S)-3-methylvalerolactone of> 90% optical purity. The corresponding 3 s lactones ...