One-pot chemoenzymatic synthesis of protected cyanohydrins |
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| Authors: | Thomas Purkarthofer Hansjörg Weber Marcel Wubbolts Peter Pöchlauer |
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| Institution: | a Research Centre Applied Biocatalysis, c/o Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria
b DSM Fine Chemicals Austria NfG GmbH and Co KG, St-Peter-Strasse 25, P.O. Box 933, A-4021 Linz, Austria |
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| Abstract: | In a chemoenzymatic one-pot reaction of ethyl cyanoformate with benzaldehyde catalyzed by the hydroxynitrile lyase from Prunus amygdalus ethoxycarbonylated (R)-mandelonitrile is formed in a highly enatioselective manner. The reaction was performed both in aqueous and organic media. 1H NMR investigations revealed a two-step procedure consisting of an enzyme-catalyzed addition of HCN, generated by hydrolysis of ethyl cyanoformate, to the aldehyde followed by ethoxycarbonylation of the free cyanohydrin in a second step |
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| Keywords: | cyanohydrins hydroxynitrile lyase (PaHNL) ethyl cyanoformate chemoenzymatic synthesis |
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