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Highly Enantioselective Access to Primary Propargylamines: 4-Piperidinone as a Convenient Protecting Group

Patrick Aschwanden, Corey R. J. Stephenson and Erick M. Carreira*

*Laboratorium für Organische Chemie, ETH Zurich, CH-8093 Zürich, Switzerland, Email:

P. Aschwanden, C. R. J. Stephenson, E. M. Carreira, Org. Lett., 2006, 8, 2437-2440.

DOI: 10.1021/ol060876w (free Supporting Information)


A highly enantioselective, catalytic three-component coupling of aldehydes, alkynes, and 4-piperidone hydrochloride hydrate affords the corresponding tertiary propargylamines in useful yields. A selective cleavage of the piperidone protecting group is possible using either ammonia/EtOH or a polymer-supported scavenger amine.

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Key Words

Propargylamines, Multicomponent Reactions, Deprotection

ID: J54-Y2006-1460