A novel copper catalyzed asymmetric N�arylation reaction between 2-substituted pyrrole heterocycles and  aryl boronate esters has been discovered.  Bis� and mono� substituted pyrroles with a carbonyl functional group were arylated with moderate to high enantioselectivities (35�90% ee) utilizing chiral diamine ligands.  A combination of base and water additives in halogenated arene solvents is critical for obtaining good yields (40�90% isolated yields). For the first time, this novel method directly forms chiral N-aryl compounds by means of cross-coupling.  The resultant compounds have potential application in the asymmetric synthesis of chiral N-aryl natural products.

Copper catalyzed asymmetric <i>N</i>–arylation of hindered pyrrole heterocycles

244th National Meeting (2012)

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Copper catalyzed asymmetric N–arylation of hindered pyrrole heterocycles