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A Rh(iii)-catalyzed regioselective intermolecular carbenoid insertion into the N -methylene Csp 3 -H bond of acyclic aliphatic amides has been achieved, taking advantage of bidentate-chelation assistance. This methodology has been successfully applied to a broad range of linear and branched-chain N -alkylamides, thus providing a practical method for the assembly of diverse beta-amino esters. Mechanism studies and density functional theory (DFT) calculations revealed that a singlet Fischer type carbene insertion via an outer-sphere pathway was involved in this N -methylene Csp 3 -H bond carbenoid insertion.

Rh(iii)-catalyzed regioselective intermolecular N-methylene Csp3–H bond carbenoid insertion

Rh(iii)-catalyzed regioselective intermolecular N-methylene Csp³–H bond carbenoid insertion