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Synfacts 2006(6): 0587-0587  
DOI: 10.1055/s-2006-934469
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Propargylamines via a Three-Component Coupling Reaction

Contributor(s): Mark Lautens, Frédéric Ménard
V. K.-Y. Lo, Y. Liu, M.-K. Wong*, C.-M. Che*
The University of Hong Kong, P. R. of China
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

A variety of propargylamines can be prepared in excellent yields by a three-component coupling reaction catalyzed by gold(III)-salen complexes in water. The chiral substituents on cyclic secondary amines transferred the chirality to the newly formed sp3 carbon center. When chiral prolinol derivatives were employed as the amine component, excellent diastereoselectivity was achieved (up to 99:1). Prolinol bearing bulky diphenyl groups afforded propargylamines 5 in 83% yield with 99:1 dr. Sensitive functionalities such as esters are not tolerated. A wide range of substrates reacted with complete aldehyde conversion.