Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group

被引:136
作者
Aschwanden, Patrick [1 ]
Stephenson, Corey R. J. [1 ]
Carreira, Erick M. [1 ]
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
D O I
10.1021/ol060876w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[graphics] We report a highly enantioselective, catalytic three-component coupling of aldehydes, alkynes, and 4-piperidone hydrochloride hydrate to afford the corresponding tertiary propargylamines in useful yields. The selective cleavage of the piperidone protecting group using either ammonia/EtOH or a polymer-supported scavenger amine furnishes primary propargylamines.
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页码:2437 / 2440
页数:4
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