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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Arena, G., Giuseppe, B., Carcone, L., Cini, E., Marras, G., Nedden, H.G., et al. (2013). Rhodium-Catalyzed Enantioselective Hydrogenation of (E)-Enol Acetate Acids. ADVANCED SYNTHESIS & CATALYSIS, 355(8), 1449-1454 [10.1002/adsc.201200934].
Rhodium-Catalyzed Enantioselective Hydrogenation of (E)-Enol Acetate Acids
Cini, Elena;Taddei, Maurizio;
2013-01-01
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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
https://hdl.handle.net/11365/45818
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