Catalyst-controlled enantioselective 1,1-arylboration of unactivated olefins

Enantioselective difunctionalization of alkenes constitutes an efficient strategy to assemble complex chiral molecules from simple racemic or achiral starting materials. Here we present an intermolecular nickel-catalysed enantioselective 1,1-arylboration of unactivated terminal alkenes. The high regio- and enantioselectivities of the reactions arise from a judicious choice of the nickel catalyst rather than the incorporation of a directing group. Moreover, excellent regioselectivities can also be obtained from the reactions of allylbenzenes. We also conducted a series of stereospecific downstream transformations for the enantioenriched secondary boronic esters. These examples represent an efficient catalyst-controlled enantioselective 1,1-difunctionalization of unactivated alkenes. Difunctionalization of alkenes can afford useful building blocks from readily available starting materials, but these reactions often show limitations in olefin scope. This work presents a catalyst-controlled enantioselective 1,1-arylboration of unactivated alkenes that is independent of directing groups.