A RuPHOX-Ru catalyzed
selective asymmetric hydrogenation of exocyclic
α,β-unsaturated ketones has been developed, furnishing
the corresponding chiral exocyclic allylic alcohols in high yields
and with up to >99.5% ee. The reaction could be performed on a
gram
scale with a relatively low catalyst loading (up to 10000 S/C) without
any loss in reaction activity and enantioselectivity. The resulting
hydrogenated products could be easily transformed to several biologically
active compounds with high asymmetric performance. The asymmetric
protocol provides an efficient methodology for the synthesis of chiral
exocyclic allylic alcohols.