Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration

We report a two-step strategy for diverse hydrofunctionalizations of aliphatic internal alkenes with high regio­selectivity and enantio­selectivity. This process comprises a copper-catalyzed asymmetric hydroboration and subsequent stereo­specific derivatizations of the secondary boronates. By this strategy, a range of compounds, such as amides, alkyl fluorides and bromides, alcohols, aldehydes, arenes, and heteroarenes, were synthesized from an internal alkene with high regio­selectivity and enantio­selectivity. Computational studies provide insight into the origins of these selectivities.