4.8 Article

Asymmetric Hydrogenation of Bicyclic Ketones Catalyzed by BINAP/IPHAN-Ru(II) Complex

Journal

ORGANIC LETTERS
Volume 12, Issue 15, Pages 3380-3383

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol101200z

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Funding

  1. Japan Science and Technology Agency (JST)
  2. Japan Society for the Promotion of Science (JSPS) [21350048]

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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.

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