Journal
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
Volume 80, Issue 6, Pages 671-679Publisher
NATL RESEARCH COUNCIL CANADA
DOI: 10.1139/V02-087
Keywords
enzyme; hydroxynitrile lyase; cyclohexanones; cyanohydrins; cis/trans-stereoselectivity
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The addition of HCN to 4-alkylcyclohexanones 1 to give cyanohydrins 2 is strongly catalyzed by hydroxynitrile lyases (HNLs). With PaHNL, from bitter almond, trans-addition occurs almost exclusively, yielding trans-2. With MeHNL, from cassava, cis-addition is preferred to give cis-2. cis-Selectivity is nearly quantitative, especially for cyclohexanones with larger 4-substituents. Comparable results with respect to the stereoselectivity were observed in the HNL-catalyzed addition of HCN to 4-alkoxycyclohexanones 3a-g. In contrast, the stereo selectivity in the HNL-catalyzed addition to 4-alkanoyloxycyclohexanones 3h-k is very poor. The transformation of cis-4-propylcyclohexanone cyanohydrin (2c) into the corresponding cis-spirotetronic acid 7 occurs without any isomerization.
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