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Synfacts 2009(11): 1263-1263  
DOI: 10.1055/s-0029-1218046
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Au-Catalyzed [3+3] Annulation of Azomethine Imines with Propargyl Esters

Contributor(s): Paul Knochel, Andreas J. Wagner
N. D. Shapiro, Y. Shi, F. D. Toste*
University of California, Berkeley, USA
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Publikationsverlauf

Publikationsdatum:
22. Oktober 2009 (online)

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Significance

The authors have reported a gold(III)-catalyzed synthesis of diazabicycles from readily available starting materials. Herein, a formal cycloaddition between alkenyl metal carbenoids and 1,3-dipoles catalyzed by gold dichloride 2-picolinate is reported for the first time. Due to minimization of steric interactions in the aurylated intermediates, the reaction proceeds with high diastereoselectivities.