Asymmetric hydrogenation of trisubstituted N-acetyl enamides derived from 2-tetralones using ruthenium-SYNPHOS catalysts: A practical synthetic approach to the preparation of β_3-adrenergic agonist SR58611A

摘要

The asymmetric hydrogenation of various trisubstituted enamides derived from 2-tetralones under mild reaction conditions using Ru-SYNPHOS catalysts is reported. This practical and clean method gives access to several chiral 2-aminotetralins derivatives in high isolated yields and enantiomeric excesses up to 95% depending on the substitution pattern of the aromatic ring and the nature of the amide moiety. In addition, the usefulness of the current method is demonstrated via a practical synthetic approach to the enantiomerically pure SR58611A compound, a potent and selective β_3-adrenergic receptor agonist.