74 CATALYTIC ASYMMETRIC HYDROGENATION OF FUNCTIONALIZED KETONES

• Kitamura M.

  Department of Chemistry, Nagoya University

• Ohkuma T.

  Department of Chemistry, Nagoya University

• Nishi T.

  Department of Chemistry, Nagoya University:Chemical Research Laboratories, Sankyo Co. Ltd.

• Takaya H.

  Department of Industrial Chemistry, Kyoto University

• Noyori R.

  Department of Chemistry, Nagoya University

Bibliographic Information

Other Title

• 74 官能基を有するケトン類の触媒的不斉水素化(口頭発表の部)

Abstract

Under the influence of the (R)- or (S)-BINAP-based Ru(II) complexes (BINAP =2,2'-bis(diphenylphosphino)-1,1'-binaphthyl), a wide range of functionalized ketones are hydrogenated in a highly enantioselective and predictable manner. The hydrogenation proceeds smoothly in alcoholic media at room temperature with initial hydrogen pressure of 40-100 atm. The substrate to catalyst mole ratio ranges from 230 to 2200. Ru complexes of the type RuX_2(binap) (X = halogen, empirical formula), Ru_2Cl_4(binap)_2N(C_2H_5)_3, or Ru(OCOR)_2(binap) are employable as catalysts, depending on the substrates. Various functionalities including dialkylamino, hydroxyl, alkoxyl, siloxyl, keto, alkoxycarbonyl, alkylthiocarbonyl, dialkylaminocarbonyl, carboxyl, etc., can act as the efficient directive group. Neighboring halogen atoms also affect strongly the stereochemical outcome. This hydrogenation method is applicable to synthesis of physioligically and pharmacologically significant agents and their intermediates such as statine, carnitine, GABOB, compactin, etc.

Journal

• Symposium on the Chemistry of Natural Products, symposium papers

  Symposium on the Chemistry of Natural Products, symposium papers 30 (0), 572-579, 1988

  Symposium on the Chemistry of Natural Products Steering Committee

Details

• CRID: 1390282681049395072
• NII Article ID: 110006678783
• DOI: 10.24496/tennenyuki.30.0_572
• ISSN: 24331856
• Text Lang: ja
• Data Source:
  • JaLC
  • CiNii Articles
• Abstract License Flag: Disallowed