Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic tertiary allylic trichloroacetimidates with anilines.

Jeffrey S Arnold, Hien M Nguyen

Department of Chemistry, University of Iowa, Iowa City, 52242, United States.

Journal of the American Chemical Society 2012 May 23

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The rhodium-catalyzed regio- and enantioselective amination of racemic tertiary allylic trichloroacetimidates with a variety of aniline nucleophiles is a direct and efficient route to chiral α,α-disubstituted allylic N-arylamines. We describe the first dynamic kinetic asymmetric transformations of racemic tertiary allylic electrophiles with anilines utilizing a chiral diene-ligated rhodium catalyst. The method allows for the formation of α,α-disubstituted allylic N-arylamines in moderate to good yields with good to excellent levels of regio- and enantioselectivity.

Citation

Jeffrey S Arnold, Hien M Nguyen. Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic tertiary allylic trichloroacetimidates with anilines. Journal of the American Chemical Society. 2012 May 23;134(20):8380-3