One-pot chemoenzymatic synthesis of protected cyanohydrins

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• 作者：Purkarthofer ; Thomas ; Skranc ; Wolfgang ; Weber ; Hansjö ; rg ; Griengl ; Herfried ; Wubbolts ; Marcel ; et. al.
• 关键词：cyanohydrins ; hydroxynitrile lyase (PaHNL) ; ethyl cyanoformate ; chemoenzymatic synthesis
• 刊名：Tetrahedron
• 出版年：2004
• 出版时间：January 12, 2004
• 年：2004
• 卷：60
• 期：3
• 页码：735-739
• 全文大小：256 K

文摘

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