title: Asymmetric hydrogenation of bicyclic ketones catalyzed by BINAP/IPHAN-Ru(II) complex.
abstract: Hydrogenation of 3-quinuclidinone and bicyclo[2.2.2]octan-2-one with a combined catalyst system of RuCl(2)[(S)-binap][(R)-iphan] and t-C(4)H(9)OK in 2-propanol afforded the chiral alcohols in 97-98% ee. 2-Diphenylmethyl-3-quinuclidinone was hydrogenated with the same catalyst to the cis alcohol with perfect diastereo- and enantioselectivity. The reaction of unsymmetrical ketones with a bicyclo[2.2.1] or -[2.2.2] skeleton gave the corresponding alcohols with high stereoselectivity.
authors.affiliation: Division of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
authors.forename: Noriyoshi
authors.initials: N
authors.lastname: Arai
authors.forename: Masaya
authors.initials: M
authors.lastname: Akashi
authors.forename: Satoshi
authors.initials: S
authors.lastname: Sugizaki
authors.forename: Hirohito
authors.initials: H
authors.lastname: Ooka
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Inoue
authors.forename: Takeshi
authors.initials: T
authors.lastname: Ohkuma