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-[(RuCl)-Cl-II{(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. (c) 2007 Elsevier B.V. All rights reserved.