Download PDF
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
Further Information

Publication History

Publication Date:
22 October 2009 (online)

    Permissions and Reprints

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.