March 3, 2026Open Access

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

Key Points

The enantioselective hydrophosphination yields α-chiral phosphorus-containing pyridine products.
Key evidence demonstrates selective activation through chiral phosphoric acid and oxazaborolidine in controlling selectivity.
Analysis of substrates with ketone and pyridine functionalities highlights crucial catalytic roles in the reactions.
Potential applications in chiral P,N-ligands stress the method's significance in asymmetric synthesis.

Abstract

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.

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

Key Points

Abstract

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