Chemical Communications 2012-12-07

Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines.

Jeffrey S Arnold, Gregory T Cizio, Drew R Heitz, Hien M Nguyen

Index: Chem. Commun. (Camb.) 48(94) , 11531-3, (2012)

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Abstract

We report the chiral diene ligated rhodium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of racemic secondary allylic trichloroacetimidates with a variety of N-methyl anilines, providing allylic N-methyl arylamines in high yields, regioselectivity, and enantiomeric excess. The rhodium-catalyzed DYKAT method addresses limitations previously associated with this particular class of aromatic nitrogen nucleophiles.