By Ojima I.
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Additional info for Applications II. Transition Metal Compounds in Organic Synthesis 1
The products can be easily converted into -hydroxy esters and 1,2-diols. 232 Some Rh or Ru catalysts with chiral phosphorus ligands such as DuPhos,230 10,57a TangPhos,116 BINAP,233 and TunePhos27 have been used for the asymmetric hydrogenation of aryl enol acetates without other functionalities (Table 5). 116 A C2-TunePhos–Ru,27 DuanPhos–Rh114 and 2–Ru38 catalysts are found to be equally effective for this transformation. Hydrogenation of cyclic enol acetates is a challenging problem. 66a Hydrogenation of acyclic enol acetates is also possible.
With trans-[RuCl2(S)-Xyl–BINAP][(S)-DAIPEN] as the metal complex, tBuOK as the base, and iPrOH as the solvent, various substituted acetophenones and acetylnaphthalenes are reduced quantitatively with high enantioselectivity and turnover numbers. Chiral BICP,67e Xylyl–PHANEPHOS,130b Xyl–P–Phos,296 Xyl–TetraPHEMP,39 SDP,134 and ligand 77161 combined with chiral diamines ligands are also effective for this catalyst system. 297 This complex can directly catalyze the hydrogenation of ketones under base-free conditions.
Using Ru–BINAP complex as catalyst and hydrochloride salt of racemic -amino -keto esters as substrate, high enantioselectivities and diasteroselectivities are achieved for the antihydrogenation product (Equation (67)). 274 For example, with an in situ formed Ru–BINAP catalyst from Ru(BINAP)(OAc)2 and HCl, a series of chiral lactones can be efficiently synthesized through asymmetric hydrogenation of 4-oxo-carboxylates (Equation (69)). (iv) Amino ketones Amino ketones or their hydrochloride salts can be effectively hydrogenated with chiral Rh or Ru catalysts (Table 15).