By Ojima I.
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Extra info for Applications II. Transition Metal Compounds in Organic Synthesis 1
189 Its cationic Ir complex has allowed the synthesis of a set of chiral aryl 2-methyl butyric acid esters with ee ranging from 95% to 99% (Equation (51)). (iii) Itaconic acids and their derivatives Many chiral phosphorus ligands have shown excellent reactivities and enantioselectivities in the Rh-catalyzed hydrogenation of itaconic acids or esters. Table 7 lists successful examples (over 95% ee) of hydrogenation of itaconic acid or dimethyl ester with different chiral phosphorus ligands. High reactivity is observed with electron-rich phosphane ligands such as BICHEP,15b Et–DuPhos,247 Ph–BPE,60 TangPhos,116 and DuanPhos114 as well as electron-deficient phosphite or phosphonite ligands such as 61,141 63,143and 74156 Some monophosphorus ligands such as MonoPhos,165,165a 80,162 and (S)-85b168 are as equally efficient as bisphosphorus chelating ligands.
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. (ii) Aliphatic ketones Asymmetric hydrogenation of simple aliphatic ketones remains a difficult area since it requires a chiral catalyst to effectively differentiate between two alkyl groups or between methyl and other alkyl group.
Et–FerroTANE–Rh catalyst, a -phenyl(monoamido)itaconate is hydrogenated completely to give the chiral monoamidosuccinate with 98% ee (Equation (53)). 6 Hydrogenation of unsaturated alcohols Asymmetric hydrogenation of unsaturated alcohols such as allylic and homoallylic alcohols was not very efficient until the discovery of the BINAP–Ru catalyst. 11b The substrate to catalyst ratio up to 48,500 can be applied, and the other double bond at the C6 and C7 positions of the substrate is not reduced.
Applications II. Transition Metal Compounds in Organic Synthesis 1 by Ojima I.