4.7 Article

An Efficient Diphosphine/Hybrid-Amine Combination for Ruthenium(II)-Catalyzed Asymmetric Hydrogenation of Aryl Ketones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 2-3, Pages 495-500

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000577

Keywords

alcohols; asymmetric catalysis; hydrogenation; N ligands; ruthenium

Funding

  1. Chinese Academy of Sciences [O7210122R0]
  2. National Natural Science Foundation of China [20620140429]
  3. Enantiotech Corp., Ltd.

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Readily available and modular hybrid amine/benzimidazole-based 1H-benzimidazole-2-methanamine (BIMA) ligands in combination with 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino) butane (DIOP) afford efficient catalytic systems for the ruthenium(II)-catalyzed asymmetric hydrogenation (AH) of a number of aryl ketones. The AH proceeds smoothly with substrate-to-catalyst (S/C) molar ratios of up to 100,000 (TOF of 6500 h(-1), 8 atm) giving chiral alcohols in up to 99% ee.

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