Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 12, Issue 16, Pages 4380-4392Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200501233
Keywords
alkynes; asymmetric catalysis; C-H activation; multicomponent reactions; organocatalysis; propargylamine
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The one-pot three-component reaction of terminal alkynes, aldehydes and secondary amines in the presence of copper(I) bromide/quinap is reported. The reaction scope has been determined and a broad variety of all three components has been used, which afforded the corresponding propargylamines in good to excellent yields and moderate to very good enantioselectivities. The reaction showed a strong positive nonlinear effect. The transformation of a propargylamine intermediate into the alkaloid (S)-(+)-coniine has also been described.
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