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氰化钠和醛及苦杏仁粗酶一锅法合成手性氰醇

Direct Use of NaCN and Aldehydes in One-Pot Asymmetric Synthesis of Cyanohydrins by Crude (R)-Oxynitrilase

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【作者】 郑祖彪姚璐璐李忠洲李新军邹新琢

【Author】 Zheng,Zubiao Yao,Lulu Li,Zhongzhou Li,Xinjun Zou,Xinzhuo(Department of Chemistry,East China Normal University,Shanghai 200062)

【机构】 华东师范大学化学系

【摘要】 直接使用固体氰化钠代替易挥发的HCN为氰源,用来源于苦杏仁的(R)-醇腈酶粗酶催化和醛的反应,并加入足量的HOAc来抑制非酶促反应和手性氰醇产物的外消旋化,一锅法合成了手性氰醇.考察了酸、(R)-醇腈酶粗酶、水、氰化钠和反应温度等因素对反应的影响.大部分反应底物的产物的产率及ee值都大于95%.该方法简单、安全、低成本、高对映选择性和收率,具有很好的应用价值.

【Abstract】 Solid sodium cyanide(NaCN) could be directly used to substitute volatile HCN as cyanide source in the one-pot asymmetric cyanohydrination of aldehydes catalyzed by crude(R)-oxynitrilase from almond with enough acetic acid to restrain the nonenzymatic reaction and racemization of chiral cyanohydrins.The effects of acid,crude(R)-oxynitrilase,volume ratio of water phase,NaCN and reaction temperature on the reaction were investigated.The yields and enantionmeric excess of most of products are higher than 95%.The proposed method has a high application value because of its simplicity,safety,and low cost as well as excellent enantioselectivities and yields.

  • 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2012年07期
  • 【分类号】O621.3
  • 【被引频次】3
  • 【下载频次】210
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