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Cobalt-Catalyzed Chemo- and Enantioselective Hydrogenation of Conjugated Enynes
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2021-06-01 , DOI: 10.1002/anie.202106566
Yanhua Hu 1 , Zhenfeng Zhang 2 , Yangang Liu 1, 2 , Wanbin Zhang 1, 2
Affiliation  

Asymmetric hydrogenation is one of the most powerful methods for the preparation of single enantiomer compounds. However, the chemo- and enantioselective hydrogenation of the relatively inert unsaturated group in substrates possessing multiple unsaturated bonds remains a challenge. We herein report a protocol for the highly chemo- and enantioselective hydrogenation of conjugated enynes while keeping the alkynyl bond intact. Mechanism studies indicate that the accompanying Zn2+ generated from zinc reduction of the CoII complex plays a critical role to initiate a plausible CoI/CoIII catalytic cycle. This approach allows for the highly efficient generation of chiral propargylamines (up to 99.9 % ee and 2000 S/C) and further useful chemical transformations.

中文翻译:

共轭烯炔的钴催化化学和对映选择性氢化

不对称氢化是制备单一对映体化合物的最有效方法之一。然而,在具有多个不饱和键的底物中相对惰性的不饱和基团的化学和对映选择性氢化仍然是一个挑战。我们在此报告了共轭烯炔的高度化学和对映选择性氢化同时保持炔键完整的协议。机理研究表明,Co II 配合物的锌还原产生的伴随的 Zn 2+在启动合理的 Co I /Co III催化循环中起着关键作用。这种方法可以高效生成手性炔丙胺(高达 99.9 % ee 和 2000 S/C)和进一步有用的化学转化。
更新日期:2021-07-19
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