Ruthenium-catalyzed asymmetric hydrogenation of N-(3,4-dihydro-2-naphthalenyl)-acetamide

The enantioselective hydrogenation of a challenging enamide (N-(3,4-dihydro-2-naphthalenyl)-acetamide, 1) bearing an endocyclic trisubstituted carbon-carbon double bond has been performed using cis–fac-delta-[Ru^IICl{(R)-(bpea)}{(S)-(BINAP)}]BF₄, cis–fac-delta-(R)-(S)-3, as catalyst achieving good conversions and enantioselectivities up to 74%. Furthermore, the study of the influence of different reaction parameters during the hydrogenation reaction has been performed, showing a strong influence of the coordinating ability of the solvent on the reaction rate.