Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5351-5353

  Dere, Ravindra T ^a   Pal, Ravindra R ^a   Patil, Prashant S ^a   Salunkhe, Manikrao M ^a  

^a INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1 BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; 1 BUTYL 3 METHYLPYRIDINIUM TETRAFLUOROBORATE; CHALCONE; DIMETHYLMALONATE; FLUORINE DERIVATIVE; IMIDAZOLE DERIVATIVE; ION; MALONIC ACID DERIVATIVE; ORGANIC COMPOUND; PYRIDINIUM DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; QUININE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; LIQUID; MICHAEL ADDITION; PHASE TRANSITION;

CINCHONA PUBESCENS;

EID: 0038007828     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01198-5     Document Type: Article

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25. 3, at room temperature, to afford the Michael adduct 3 in 96% yield and 61% ee (Table 1, entry 1). Among the organic solvents tried, DMSO proved to be most effective in this reaction.
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27. 13C NMR (MeOH) δ 22.65, 26.29, 28.49, 39.57, 53.58, 57.12, 62.57, 64.98, 66.51, 71.06, 103.22, 118.18, 122.14, 123.64, 127.85, 129.50, 129.95,131.35, 132.37, 134.78, 135.61, 136.66, 138.99, 142.68, 145.22, 145.59, 146.39, 148.75, 160.55.
28. 4, filtered, concentrated, and purified by flash chromatography (silica gel, dichloromethane) to afford the Michael adduct.