(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.

Enantioselective catalysis in water : Mukaiyama-aldol condensation promoted by copper complexes of bisoxazolines supported on poly(ethylene glycol) / M. Benaglia, M. Cinquini, F. Cozzi, G. Celentano. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 2:22(2004), pp. 3401-3407.

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

M. Benaglia
Primo
;
M. Cinquini
Secondo
;
F. Cozzi
Penultimo
;
G. Celentano
Ultimo
2004

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.
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/144637
Citazioni
  • ???jsp.display-item.citation.pmc??? 1
  • Scopus 39
  • ???jsp.display-item.citation.isi??? 34
social impact