Rh(III)-Catalyzed C–H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors

A Rh­(III)-catalyzed
C–H bond addition/primary amine-promoted
cyclization of bis-Michael acceptors is reported. The C–H bond
addition step occurs with high chemoselectivity, and the subsequent
intramolecular Michael addition, mediated by a primary amine catalyst,
sets three contiguous stereocenters with high diastereoselectivity.
A broad range of directing groups and both aromatic and alkenyl C–H
bonds were shown to be effective in this transformation, affording
functionalized piperidines, tetrahydropyrans, and cyclohexanes.