Direct use of NaCN and aldehydes in one-pot asymmetric synthesis of cyanohydrins by crude (R)-oxynitrilase

doi:10.6023/cjoc1112271

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (07): 1284-1289.DOI: 10.6023/cjoc1112271 Previous Articles Next Articles

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氰化钠和醛及苦杏仁粗酶一锅法合成手性氰醇

郑祖彪, 姚璐璐, 李忠洲, 李新军, 邹新琢

华东师范大学化学系上海 200062

收稿日期:2011-12-27 修回日期:2012-02-21 发布日期:2012-03-09
通讯作者: 邹新琢 E-mail:xzzou@chem.ecnu.edu.cn

Direct use of NaCN and aldehydes in one-pot asymmetric synthesis of cyanohydrins by crude (R)-oxynitrilase

Zheng Zubiao, Yao Lulu, Li Zhongzhou, Li Xinjun, Zou Xinzhuo

Department of Chemistry, East China Normal University, Shanghai 200062

Received:2011-12-27 Revised:2012-02-21 Published:2012-03-09

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.

Key words: NaCN, (R)-oxynitrilase, one-pot, asymmetric synthesis, aldehydes, cyanohydrin

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Zheng Zubiao, Yao Lulu, Li Zhongzhou, Li Xinjun, Zou Xinzhuo. Direct use of NaCN and aldehydes in one-pot asymmetric synthesis of cyanohydrins by crude (R)-oxynitrilase[J]. Chin. J. Org. Chem., 2012, 32(07): 1284-1289.

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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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