Catalyst-Controlled Regio- and Enantioselective Hydrophosphination of α,β-Unsaturated Pyridyl Ketones.

Here, we present an enantioselective and regioselective hydrophosphination of α,β-unsaturated substrates that feature both ketone and pyridine bifunctional groups. Interestingly, the activation of pyridine and ketone functionalities is selectively achieved through chiral phosphoric acid and oxazaborolidine, respectively. The regioselectivity of the phosphine nucleophiles toward the products can be well controlled by the choice of catalysts. In addition, the α-chiral phosphorus-containing pyridine products exhibit potential applications as chiral P,N-ligands.