Asymmetric multicomponent copper catalyzed synthesis of chiral propargylamines
- 作者：Federica Colombo ; Maurizio Benaglia ; Simonetta Orl ; i ; Fabio Usuelli
- 关键词：Multicomponent reactions ; Chiral copper(I) complexes ; Asymmetric catalysis ; Phenylacetylene addition ; Chiral propargylamines
- 刊名：Journal of Molecular Catalysis A ; Chemical
- 出版年：2006
- 期刊代码：57_13811169
- 类别：ch
- 出版时间：15 December 2006
- 卷：260
- 期：1-2
- 页码：128-134
- 文件大小：364 K
摘要
A three-component stereoselective reaction between an aldehyde, an amine and phenylacetylene to afford optically active propargyl amines in good yields was developed. The reaction is catalysed by copper complexes of enantiomerically pure bis-imines. The best results were obtained with imines readily prepared in very high yields from the commercially available binaphtyl diamine.
A very simple experimental procedure at room temperature allowed to obtain optically active propargyl amines in very good yields and enantioselectivity up to 75%. The extremely simple methodology and the mild reaction conditions, as well as the possibility of a modular approach for developing new and more efficient bis-imine-based chiral ligands make the present methodology very attractive.