Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes
Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes
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DOI：
10.1021/jo052481g
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发表时间：
2006-03-03
影响因子：
3.6
通讯作者：
Celentano, G
中科院分区：
文献类型：
--
作者：
Colombo, F;Benaglia, M;Celentano, G
[图表]研究了芳基和烷基乙炔衍生物对亚胺的立体选择性加成。该反应由对映体纯的双亚胺的铜络合物催化，该双亚胺容易地从市售的联萘二胺以非常高的产率制备。一个非常简单的实验程序允许在室温下获得光学活性炔丙胺在高产率和对映体选择性。有趣的是，双亚胺/铜（I）配合物能够促进直接，对映选择性，催化加成到烷基乙炔亚胺。研究了催化剂用量和其它反应参数对立体化学转化结果的影响。非常方便的方法，温和的反应条件，以及开发新的和更有效的基于双亚胺的手性配体的模块化方法的可能性，使得本方法非常有吸引力。
[GRAPHICS]The stereoselective addition of aryl- and alkylacetylene derivatives to imines was studied. The reaction is catalyzed by copper complexes of enantiomerically pure bisimines, readily prepared in very high yields from the commercially available binaphthyl diamine. A very simple experimental procedure allowed to obtain at room temperature optically active propargylamines in high yields and enantio selectivity. Interestingly, bisimine/copper(I) complexes were able to promote the direct, enantio selective, catalytic addition to imines of alkylacetylenes. The effects of catalyst loading and other reaction parameters on the stereochemical outcome of the transformation were investigated. The extremely convenient methodology, the mild reaction conditions, and the possibility of a modular approach for developing new and more efficient bisimine-based chiral ligands make the present methodology very attractive.