Asymmetric hydrogenation of bicyclic ketones catalyzed by BINAP/IPHAN-Ru(II) complex

Noriyoshi Arai; Masaya Akashi; Satoshi Sugizaki; Hirohito Ooka; Tsutomu Inoue; Takeshi Ohkuma

doi:10.1021/ol101200z

Asymmetric hydrogenation of bicyclic ketones catalyzed by BINAP/IPHAN-Ru(II) complex

Org Lett. 2010 Aug 6;12(15):3380-3. doi: 10.1021/ol101200z.

Authors

Noriyoshi Arai¹, Masaya Akashi, Satoshi Sugizaki, Hirohito Ooka, Tsutomu Inoue, Takeshi Ohkuma

Affiliation

¹ Division of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.

PMID: 20670005
DOI: 10.1021/ol101200z

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.