Synthesis of enantiomerically enriched propargylamines by copper-catalyzed addition of alkynes to enamines

被引:124
作者
Koradin, C [1 ]
Gommermann, N [1 ]
Polborn, K [1 ]
Knochel, P [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
关键词
alkynes; amines; asymmetric catalysis; C-H activation; copper catalysis;
D O I
10.1002/chem.200204691
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first copper(I) bromide/ Quinap-catalyzed synthesis of enantiomerically enriched propargylamines by addition of alkynes to enamines is reported. Various functionalized terminal alkynes add smoothly to N-protected enamines to afford the corresponding amines in good to high yields and moderate to good enantiomeric excesses. The influence of the metal salt, the ligand, and the protecting group on the conversion, the reaction rate, and the stereoselectivity of the reaction are investigated. The scope of the reaction and further transformations of the resulting propargylamines (deprotection, Pauson-Khand reaction) are also described.
引用
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页码:2797 / 2811
页数:15
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