Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction |
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Authors: | Gommermann Nina Knochel Paul |
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Affiliation: | Department Chemie, Ludwig-Maximilians-Universit?t, Butenandtstrasse 5-13, Haus F, 81377 München, Germany. |
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Abstract: | 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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Keywords: | alkynes asymmetric catalysis C?H activation multicomponent reactions organocatalysis propargylamine |
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