醛酮的不对称硅氰化反应研究进展

doi:10.6023/cjoc201505045

摘要/Abstract

羰基化合物的不对称氰醇化反应是当前不对称催化领域里的一个研究热点. 具有光学活性的氰醇是有机合成的重要中间体, 通过官能团转化可以很容易制备出一些在天然产物和化学制药中具有重要意义的手性化合物, 如β-氨基醇、α-氨基酸和α-羟基酸等. 目前, 不对称催化的三甲基氰硅烷与醛酮的加成反应作为手性氰醇的主要化学合成方法受到人们的广泛关注, 而反应体系中采用的手性配体与Lewis酸是控制这类反应的效能和立体选择性的关键, 因此, 主要就三甲基氰硅烷和醛酮不对称加成反应中催化体系的发展作了一个简要的述评.

关键词: 手性催化, 不对称硅氰化反应, 醛酮, 手性配体

The asymmetric cyanation of carbonyl compounds occupies a hot research topic in current catalytic chemistry. Optically pure cyanohydrins are important synthetic intermediates which can be easily transformed into optically pure compounds, including β-aminoalcohols, α-amino acids and α-hydroxy acids, thus exihibits fundermental utility in many natural products and chemical pharmacy synthesis. Presently, the asymmetric silylcyanation of trimethylsilyl cyanide with aldehydes and ketones represents a main approach for optically pure cyanohydrin synthesis. The complex of chiral ligand and Lewis acid is the key element that determines the efficiency and controls the stereochemisty of these reactions. This review briefly summarizes the development of asymmetric catalysis empolyed in the chiral cyanohydation of aldehydes and ketones using trimethylsilyl cyanide as the cyanating agent.

Key words: chiral catalysis, asymmetric silylcyanation, aldehyde and ketone, chiral ligand

引用此文

傅颖, 侯博, 赵兴玲, 杜正银, 胡雨来. 醛酮的不对称硅氰化反应研究进展[J]. 有机化学, 2015, 35(12): 2507-2521.

Fu Ying, Hou Bo, Zhao Xingling, Du Zhengyin, Hu Yulai. Progress on the Asymmetric Silylcyanation of Aldehydes and Ketones[J]. Chin. J. Org. Chem., 2015, 35(12): 2507-2521.

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