Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts.
Seventeen organocatalyts were tested for their ability to catalyst the addition of thiophenols to chalcones in [bmim]PF6. The products were isolated in high yield after a short reaction time, but no stereoselectivity was observed. The reactions also proceeded (without any stereoselectivity) in four other ionic liquids. In contrast, 16% and 26% ee were observed when L-proline and cinchonine, respectively, were used as the catalysts in CH2Cl2. Addition of thiophenols is also catalysed by HCl, as well as D-mandelic and L-tartaric acids. Addition of thiophenols to chalcones also occurred in neat ionic liquids, without any additional catalyst, but the rate of the reaction depended considerably on the structure of ionic liquid. The scope of the non-catalysed reaction in ionic liquids was tested by the reactions of 5 different thiols and 3 different alpha-enones.
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina, SK-842 15, Bratislava, Slovakia.
Mária
M
Meciarová
Stefan
S
Toma
Peter
P
Kotrusz
D002384:Catalysis; D003516:Cycloparaffins / Q000138:chemical synthesis / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009930:Organic Chemicals / Q000737:chemistry*; D012997:Solvents; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D003516:Cycloparaffins; D006843:Hydrocarbons, Chlorinated; D009930:Organic Chemicals; D012997:Solvents; D013438:Sulfhydryl Compounds