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Rhodium‐Catalyzed Enantioselective Hydrogenation of ( E )‐Enol Acetate Acids
Author(s) -
Arena Giada,
Barreca Giuseppe,
Carcone Luca,
Cini Elena,
Marras Giovanni,
Nedden Hans G.,
Rasparini Marcello,
Roseblade Stephen,
Russo Adele,
Taddei Maurizio,
ZanottiGerosa Antonio
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200934
Subject(s) - rhodium , chemistry , catalysis , enantioselective synthesis , enol , asymmetric hydrogenation , ton , microwave irradiation , organic chemistry , hydrogen , bar (unit) , medicinal chemistry , physics , fishery , meteorology , biology
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.