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Synfacts 2011(5): 0520-0520  
DOI: 10.1055/s-0030-1259826
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Stereoselective Synthesis of Azacyclic Compounds

Contributor(s): Mark Lautens, Hasnain A. Malik
A. M. Jadhav, S. Bhunia, H.-Y. Liao, R.-S. Liu*
National Tsing-Hua University, Hsinchu and National Taipei University of Education, Taiwan, P. R. of China
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

The authors report a metal-catalyzed stereoselective redox/[2+2+1] cycloaddition cascade sequence. From achiral commercially available starting materials, complex azacyclic compounds can be formed in a one-step protocol. The yields from this procedure are moderate to good and a variety of electron-rich alkenes can be employed. The authors also demonstrate that the reaction is tolerant of a wide array of substitution patterns on the phenyl moiety of the nitrobenzene starting material. Theoretical and experimental mechanistic investigations are performed.