Ligand Control of Geometric Selectivity in Protosilylation of Acyclic α-Substituted α,β-Unsaturated N-Sulfinyl Ketimines

The copper(I)-catalyzed silyl conjugate addition to α-substituted α,β-unsaturated N-tert-butanesulfinyl ketimines presents a facile approach for the synthesis of acyclic β,β-disubstituted enesulfinamides. By varying the ligand associated with the copper catalysts, it is feasible to selectively produce multisubstituted enesulfinamides with either (Z)- or (E)-configuration, thereby facilitating their effective use in the stereoselective nucleophilic reactions to construct less accessible acyclic quaternary or tetrasubstituted stereocenters, encompassing both absolute configurations.