Catalytic Enantioselective Diboration of 1,2-Dihydropyridines

Dihydropyridines undergo enantioselective 1,4-diboration in the presence of a chiral Pt-based catalyst. The resulting diboryl piperidines can undergo diverse stereospecific cross-couplings, allowing the construction of an array of different substituted chiral piperidines. Density functional theory (DFT) calculations provide insight into a plausible diboration pathway that involves a platinum-centered reaction between coordinated B₂L₂ reagent and the diene to furnish an intermediate π-allyl platinum complex.