Regio- and Enantio-selective Reduction ofα,γ-Diketones by Fermenting Bakers’ Yeast
- 1 October 1986
- journal article
- research article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 50 (10) , 2499-2502
- https://doi.org/10.1080/00021369.1986.10867768
Abstract
Reduction of various numbers of 2,4-alkanediones by fermenting bakers’ yeast has been found to be highly regio- and enantio selective, resulting in the formation of 2-hydroxy-4-alkanones. In some cases, optical purities of the products exceeded over 99% as determined by HPLC analysis of MTPA esters. The highest yield was obtained when the reaction was carried out at,pH 8 with low substrate concentration. As the representative β-hydroxyketones, the absolute configuration of ( + )-2-hydroxy-4-octanone (2d) and ( + )-3-hydroxy-1-phenyl-1-butanone (2h) was unambiguously determined to be (S) by comparing the specific rotation of diol derivatives with those of authentic specimens.This publication has 5 references indexed in Scilit:
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