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Enantioselective, Copper(I)-Catalyzed Three-Component Reaction for the Preparation of Propargylamines

Nina Gommermann, Christopher Koradin, Kurt Polborn, Paul Knochel*

*Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany, Email: paul.knochelcup.uni-muenchen.de

N. Gommermann, C. Koradin, K. Polborn, P. Knochel, Angew. Chem. Int. Ed., 2003, 42, 5763-5766.

DOI: 10.1002/anie.200352578 (free Supporting Information)


Abstract

A wide range of chiral propargylamines can be prepared in a one-pot three-component reaction between an alkyne, an aldehyde and a secondary amine at room temperature in the presence of CuBr and (R)-quinap in good yield and good enantioselectivity. Remarkably, the copper-catalyzed reaction is highly diastereoselective if a chiral amine or aldehyde is used.

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Key Words

alkynes, asymmetric catalysis, C-H activation, multicomponent reactions, propargylamines


ID: J06-Y2003-1120