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Letter

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

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

Laboratorium fr Organische Chemie, ETH Zurich, CH-8093 Zrich, Switzerland

Org. Lett., 2006, 8 (11), pp 2437–2440

DOI: 10.1021/ol060876w

Publication Date (Web): May 5, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, carreira@org.chem.ethz.ch

Abstract

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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Published In Issue May 25, 2006
Received April 11, 2006

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Letter

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Syntheses of Kapakahines B and F

Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring Expansion

Gold(I)-Catalyzed Coupling Reactions for the Synthesis of Diverse Small Molecules Using the Build/Couple/Pair Strategy

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