Synfacts 2009(7): 0752-0752  
DOI: 10.1055/s-0029-1217268
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Substituted Dienes through Isomerization of Allenamides

Contributor(s): Mark Lautens, Jane Panteleev
R. Hayashi, R. P. Hsung*, J. B. Feltenberger, A. G. Lohse
University of Wisconsin, Madison, USA
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Publication History

Publication Date:
22 June 2009 (online)


The authors report a regioselective rearrangement of allenamides yielding dienes bearing amido groups. Although allenes are known to undergo such isomerizations, the authors demonstrate an application to the stereo­selective synthesis of products which are difficult to obtain through other means. The yields observed are good for a range of substituted analogues and the regioselectivity achieved is excellent.