By Ojima I.
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Additional resources for Applications II. Transition Metal Compounds in Organic Synthesis 1
57a In contrast to the many successful examples for hydrogenation of the parent itaconic acid or its dimethyl ester, only a few ligands have been reported to be efficient for the hydrogenation of -substituted itaconic acid derivatives. 5 atm H2a THF, Rt, 20 psi H2 THF, Rt, 20 psi H2 96 (S) 94 (R) 97 (S) 95 (S) 99 (R) 96 (S) >99 (S) 69b 246 247 116 247 116 114 a 10 mol% of NaOMe is added. efficient for the hydrogenation of several -substituted itaconic acid derivatives. Some examples are shown in Table 8.
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.
In the case of hydrogenation of 2-arylpropionic acids, high hydrogenation pressure and low temperature are required to achieve good enantioselectivity. 90 ð41Þ ð42Þ ð43Þ ð44Þ ð45Þ C–H Bond Formation by Asymmetric and Stereoselective Hydrogenation In contrast to successful results obtained with Ru catalysts, few systems have been reported on the Rh-catalyzed hydrogenation of ,-unsaturated carboxylic acids. 79 The aminoalkyl side chain of the ligand is important to maintain the high reactivity and enantioselectivity.
Applications II. Transition Metal Compounds in Organic Synthesis 1 by Ojima I.