Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis
Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis
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DOI：
10.1126/science.277.5328.936
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发表时间：
1997-08-15
期刊：
影响因子：
56.9
通讯作者：
Jacobsen, EN
中科院分区：
文献类型：
--
作者：
Tokunaga, M;Larrow, JF;Jacobsen, EN
环氧化物是有机合成的通用构件。然而，末端环氧化物可以说是这些化合物中最重要的子类，并且不存在以对映体纯形式生产它们的通用且实用的方法。末端环氧化物可以以外消旋混合物的形式非常便宜地获得，并且由于方法经济且操作简单，因此动力学拆分是生产光学活性环氧化物的一种有吸引力的策略。易于获得的合成催化剂（手性钴基萨伦配合物）已用于末端环氧化物的有效不对称水解。该过程使用水作为唯一的试剂，不添加溶剂，并且可回收催化剂的负载量低（
Epoxides are versatile building blocks for organic synthesis. However, terminal epoxides are arguably the most important subclass of these compounds, and no general and practical method exists for their production in enantiomerically pure form. Terminal epoxides are available very inexpensively as racemic mixtures, and kinetic resolution is an attractive strategy for the production of optically active epoxides, given an economical and operationally simple method. Readily accessible synthetic catalysts (chiral cobalt-based salen complexes) have been used for the efficient asymmetric hydrolysis of terminal epoxides. This process uses water as the only reagent, no added solvent, and low loadings of a recyclable catalyst (