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Keywords:

  • cinchona-alkaloid modified catalysts;
  • enantioselective hydrogenation;
  • heterogeneous modified catalysts;
  • hydrogenation of functionalized ketones;
  • tartrate-modified nickel catalysts

Abstract

The state of the art for the enantioselective hydrogenation applying chirally modified heterogeneous catalysts is reviewed with emphasis on new developments between 1997 and 2002. Discussed are various combinations of metal–modifier–substrate which give enantioselectivities useful for synthetic applications. The three most important asymmetric catalysts types are nickel catalysts modified with tartaric acid, useful for β-functionalized ketones with ees up to 98.6%, platinum catalysts modified with cinchona alkaloids and related modifiers, successful for α-functionalized ketones with ees up to 98% and palladium catalysts modified with cinchona alkaloids which achieve ees up to 94% for selected activated C[DOUBLE BOND]C bonds. Mechanistic investigations comprising surface science and spectroscopic studies often combined with computational modeling as well as kinetic studies are summarized and the various mechanistic models are discussed.