Arylamine-Catalyzed Enamine Formation: Cooperative Catalysis with Arylamines and Acids


  • We acknowledge Miami University and National Science Foundation Career program (CHE-1056420) for financial support. K.W. acknowledges NSF grant (CHE-0722547). We would like to thank Prof. D. Toste and co-workers for providing useful information of the chiral counterion approach.


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Powerful combination: Arylamines and metal Lewis acids are used as catalysts in the highly chemo- and enantioselective three-component inverse-electron-demand aza-Diels–Alder reaction of cyclic ketones with enones. The enantioselectivity is introduced by a simple chiral anion (see scheme). Arylamines can also serve as effective enamine catalysts in combination with either a metal Lewis acid or a Brønsted acid.