American Chemical Society
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Asymmetric Hydrogenation of Bicyclic Ketones Catalyzed by BINAP/IPHAN−Ru(II) Complex

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journal contribution
posted on 2010-08-06, 00:00 authored by Noriyoshi Arai, Masaya Akashi, Satoshi Sugizaki, Hirohito Ooka, Tsutomu Inoue, Takeshi Ohkuma
Hydrogenation of 3-quinuclidinone and bicyclo[2.2.2]octan-2-one with a combined catalyst system of RuCl2[(S)-binap][(R)-iphan] and t-C4H9OK 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.