The combination of organo-aminocatalysis with metal Lewis acid catalysis has emerged as a powerful tool in organic synthesis. However, acid-base quenching reaction leading to catalyst inactivation has slowed down the growth of this new research area. In this presentation, we demonstrate that the utilization of arylamines as aminocatalysts, replacing the chiral aliphatic amines generally used in organocatalysis, can solve this problem. Via this approach, the successful development of challenging asymmetric three-component inverse-electron-demand aza-Diels-Alder reaction of ketones with enones was achieved. Our findings that aromatic amines can serve as effective enamine catalyst through incorporation with either a metal Lewis acid or a Br�nsted acid provide new tools in organic synthesis and catalysis, and will facilitate the discovery of new carbon-carbon and carbon-heteroatom bond-forming reactions.

Arylamines as enamine catalysts: A new strategy for cooperative catalysis

245th National Meeting (2013)

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