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Practical Highly Enantioselective Synthesis of Propargylamines through a Copper-Catalyzed One-Pot Three-Component Condensation Reaction

✍ Scribed by Nina Gommermann; Paul Knochel

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
277 KB
Volume
12
Category
Article
ISSN
0947-6539

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✦ Synopsis

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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