CuH-Catalyzed Asymmetric Reduction of α,ß-Unsaturated Carboxylic Acids to ß-Chiral Aldehydes.

ABSTRACT

The copper hydride (CuH)-catalyzed enantioselective reduction of α,ß-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of ß-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.