Canadian Journal of Chemistry

Enzymes in organic synthesis. 14. Stereoselective horse liver alcohol dehydrogenase catalyzed oxidations of diols containing a prochiral centre and of related …

JB Jones, KP Lok

Index: Jones,J.B.; Lok,K.P. Canadian Journal of Chemistry, 1979 , vol. 57, p. 1025 - 1032

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Citation Number: 28

Abstract

The asymmetric synthetic potential of horse liver alcohol dehydrogenase catalyzed oxidations of variously 3-substituted pentane-1, 5-diols has been further delineated. The oxidations proceed with enantiotopic selectivity to give the corresponding (3 S)-3-substituted valerolactones of up to 78% ee. The reactions occur via initial oxidation of the pro-S hydroxyethyl group, with the initially-formed hydroxyaldehydes undergoing further in situ ...