Rhodium-Catalyzed Reductive Coupling of Enones and Aromatic Aldehydes

Significance

As an extension on previous work concerning the reductive coupling of α,β-unsat­urated esters with aldehydes or ketones (J. Am. Chem. Soc. 2005, 127, 6972), the authors now describe the rhodium-catalyzed reductive coupling of enones with aromatic aldehydes. The product β-hydroxyketones were obtained with high anti selectivity and enantioselectivity. A cyclic transition state on the rhodium active site is proposed for the reaction, whereby the Re-face of the enolate carbon atom could attack the Re-face of the aldehyde carbon atom leading to the observed stereochemistry.