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Density functional theory (DFT) has provided a detailed mechanistic picture for the redox neutral nickel(II)-catalyzed arylative cyclization reactions of a tethered allene-ketone with arylboronic acids. A mechanistic rationale for the high diastereo- and enantioselectivity achieved experimentally at high reaction temperature was uncovered through modeling the reaction with a chiral ligand and the predicted stereochemical outcome corroborates with experimental results. An unprecedented mechanism for the base-free organoboron transmetalation was revealed and the regioselectivity of migratory ins...

Transition metal-catalysed reactions represent a valuable tool for the construction of sp3-rich, stereodefined molecular scaffolds in a single synthetic step. Though these reactions have garnered considerable attention over the last few decades, recent literature indicates that the fractional sp3 character of drug-like molecules has gradually decreased over the last twenty years. This is in part, due to the increased use of transition metal-catalysed cross-coupling reactions such as the Heck and Suzuki–Miyaura reactions, which allow for the preparation of flat, aromatic molecules in a single...