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)

概要

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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.
天然有機化合物討論会の論文
1988-09-26