Enantioselective catalysis in water: Mukaiyama-aldol condensation promoted by copper complexes of bisoxazolines supported on poly(ethylene glycol)

Abstract

(S)-3-Phenyl-2-aminopropanol-derived bisoxazolines supported on a modified poly(ethylene glycol) were shown to be effective Cu(II) ligands for the enantioselective Mukaiyama-aldol condensation of various aldehydes with the trimethylsilyl keteneacetal of methyl isobutyrate carried out in water. Enantiomeric excesses comparable to those obtained with nonsupported ligands in the same solvent were observed. The solubility of the ligand in water, ensured by the presence of the polymeric support, allowed a very convenient catalyst-recycling procedure involving simple removal of the reaction product by extraction in Et₂O and addition of fresh reagents to the catalyst-containing aqueous solution. The chemical and stereochemical efficiency of the catalyst was only marginally eroded over its use in three reaction cycles.