Abstract: Chirally modified metal catalysts are one of most developed and promising heterogeneous enantioselective catalysts. The recent progress of the enantioselective hydrogenation of β-ketoesters on tartaric acid modified nickel catalysts, the enantioselective hydrogenation of α-ketoesters using cinchona alkaloid modified platinum, and the enantioselective hydrogenation of carbon-carbon and carbon-nitrogen double bonds using cinchona alkaloid modified palladium catalysts are summarized. The influential factors of the catalyst systems are briefly introduced, and the enantioselection mechanism in tartaric acid modified nickel catalysts and cinchona alkaloids modified platinum catalysts are also discussed. In addition, further research work in heterogeneous asymmetric hydrogenation should be focused on development of high efficiency catalysts and investigation of reaction mechanism.

Key words: heterogeneous catalysis, enantioselective hydrogenation, chiral catalyst, tartaric acid, cinchona alkaloids

摘要： 手性修饰金属催化剂是最具发展潜力的多相不对称催化剂之一。本文综述了近年来三个具有代表性的多相不对称氢化反应体系的研究进展，即酒石酸修饰镍催化剂催化β-酮酯不对称加氢体系、金鸡纳生物碱修饰铂催化剂催化α-酮酯不对称加氢体系以及金鸡纳生物碱修饰钯催化剂催化C=C和C=N双键不对称加氢体系。概述了催化体系的影响因素，探讨了酒石酸及金鸡纳生物碱修饰型催化剂的手性识别机理模型。指出开发高效催化剂，修正或提出手性识别机理模型仍是今后多相不对称催化氢化反应研究的方向。

关键词: 多相催化, 不对称氢化, 手性催化剂, 酒石酸, 金鸡纳生物碱