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Rhodium‐Catalyzed Enantioselective Hydrogenation of (E)‐Enol Acetate Acids
Authors:Giada Arena  Giuseppe Barreca  Luca Carcone  Elena Cini  Giovanni Marras  Hans G Nedden  Marcello Rasparini  Stephen Roseblade  Adele Russo  Maurizio Taddei  Antonio Zanotti‐Gerosa
Abstract:The novel rhodium complex Rh(S)‐Phanephos(cod)]‐catalyzed hydrogenation of disubstituted (E)‐enol acetate carboxylic acids is reported. The catalytic cycle works under 30 bar of hydrogen under conventional heating giving different 3‐acetoxy‐2,3‐disubstituted carboxylic acids with ee ≥90%. Hydrogenation occurred also under microwave dielectric heating without eroding the enantioselectivity but improving the overall efficiency of the process. With microwaves, hydrogen pressure and reaction time required for complete hydrogenation dropped to 5 bar and 30 min, respectively. The best performance of this catalyst under microwave irradiation was TON 100, TOF 196 h−1 with ee 99% on a 6‐g scale.
Keywords:asymmetric catalysis  carboxylic acids  hydrogenation  microwave heating  phosphane ligands
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