Rh(I)-catalyzed enantioselective hydrogenation of α-substituted ethenylphosphonic acids.
A class of chiral Rh(I) catalysts containing monodentate phosphorous acid diesters tautomerized from the corresponding secondary phosphine oxides was discovered by serendipitous hydrolysis of phosphoramidite ligands. The evolved catalysts demonstrated unprecedented enantioselectivities (98-99% ee) and high catalytic activities (as low as 0.01 mol% catalyst loading) in asymmetric hydrogenations of a wide variety of α-aryl-/alkyl-substituted ethenylphosphonic acids, providing a facile approach to the corresponding enantiopure phosphonic acids with significant biological importance.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P R China.
Kaiwu
K
Dong
Zheng
Z
Wang
Kuiling
K
Ding
D002384:Catalysis; D006865:Hydrogenation; D006868:Hydrolysis; D008024:Ligands; D008958:Models, Molecular; D009943:Organophosphorus Compounds / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D010757:Phosphorous Acids / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D008024:Ligands; D009943:Organophosphorus Compounds; D010087:Oxides; D010720:Phosphines; D010757:Phosphorous Acids; C434331:phosphoramidite; D012428:Ruthenium; C044646:phosphine