By Ojima I.
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Additional info for Applications II. Transition Metal Compounds in Organic Synthesis 1
24a The chiral diol can be obtained with 98% ee and a substrate-to-catalyst ratio of 10,000. 3i Although the alkoxy group of the substrates do not participate in coordination with the Ru catalyst, they possess a significant stereo-directing ability in achieving high enantioselectivity. For example, methoxyacetophenone is hydrogenated with an Ru-(R)-XylBINAP/(R)-DIPEN complex to provide the corresponding (R)-diol with 95% ee. 12a,261,278 Hydrogenation of ortho-haloaryl ketones can be catalyzed by the Ru– BINAP system with excellent ee’s.
E/Z ¼ 1 : 1. c S/C ratio ¼ 10,000. b derivatives, achieving high enantioselectivities for the (Z)-isomeric substrates is more important for the practical synthesis of chiral 3-aryl-3-amino acids via the asymmetric hydrogenation. Few efficient ligands have been reported for the hydrogenation of (Z)-3-aryl-3-(acylamino)acrylates. Xylyl–BINAPO–Ru catalyst,140 TangPhos–Rh catalyst,115 BINAPINE–Rh,113 and hybrid ferrocenylphosphine–phosphoramidite 75156a are found to be effective for the reactions of a variety of (Z)-3-aryl-3-(acylamino)acrylates.
Some other C2-symmetric ligands such as BPE,262 BisP* ,263 and PHANEPHOS,130a are also effective. 81 Some examples of the efficient hydrogenation of 3-oxobutanoic acid esters with different chiral phosphorus ligand systems are listed in Table 12. 12 Many other atropisomeric ligands have provided better enantioselectivity for this substrate, as shown in Table 13. 12a,264,264a When a coordinative functional group such as a chloride or methoxy group exists in the proximity of the carbonyl group of a -keto ester, lower enantioselectivity appears to be observed due to the competition of two different coordination patterns.