Data di Pubblicazione:
2000
Citazione:
Soluble-polymer-supported synthesis of beta-lactams on a modified poly(ethylene glycol) / R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 6:1(2000), pp. 133-138.
Abstract:
A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of β-lactams. The monomethylether of PEG (MeOPEG) with an average Mw of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several β-lactams by enolate/imine condensation and ketene/ imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the β-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Imines; Lactams; Polymer-supported synthesis; Polymers
Elenco autori:
R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi
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