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Synfacts 2008(7): 0736-0736  
DOI: 10.1055/s-2008-1078458
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Propargylic Substitution of Propargylic Acetates with Amines

Contributor(s): Mark Lautens, Valentina Aureggi
G. Hattori, H. Matsuzawa, Y. Miyake, Y. Nishibayashi*
The University of Tokyo, Japan
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Publikationsverlauf

Publikationsdatum:
20. Juni 2008 (online)

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Significance

The development of the copper-catalyzed enantioselective propargylic substitution of propargylic acetates with amines is reported. The corresponding propargylic amines are obtained in moderate to excellent yields with up to 89% ee. The protocol described may provide an efficient novel synthetic method for the preparation of chiral propargylic amines which are versatile intermediates for the synthesis of various biologically active compounds.