A number of N-benzylic protecting groups and allylic substituents have been investigated for the rearrangement, promoted by CuCl-TMEDA, of N-allyl-2,2-dihaloamides to 3,4-disubstituted gamma-lactams. An appreciable chiral induction was observed at the C-4 site when alpha-phenylethylamine was used as a chiral protecting group, while an unexpected Diels-Alder reaction occurred when using a 2-furyl-methyl protection. This rearrangement has been applied to the synthesis of pilolactam, a drug with muscarinic activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-allyl-N-benzyl-2,2-dihaloamides to gamma-lactams. Application to the stereoselective synthesis of pilolactam / Ghelfi, Franco; Bellesia, Franco; Forti, Luca; G., Ghirardini; Grandi, Romano; Libertini, Emanuela; M. C., Montemaggi; Pagnoni, Ugo Maria; Pinetti, Adriano; L., De Buyck; A. F., Parson. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 55:(1999), pp. 5839-5852. [10.1016/S0040-4020(99)00247-1]

The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-allyl-N-benzyl-2,2-dihaloamides to gamma-lactams. Application to the stereoselective synthesis of pilolactam.

GHELFI, Franco;BELLESIA, Franco;FORTI, Luca;GRANDI, Romano;LIBERTINI, Emanuela;PAGNONI, Ugo Maria;PINETTI, Adriano;
1999

Abstract

A number of N-benzylic protecting groups and allylic substituents have been investigated for the rearrangement, promoted by CuCl-TMEDA, of N-allyl-2,2-dihaloamides to 3,4-disubstituted gamma-lactams. An appreciable chiral induction was observed at the C-4 site when alpha-phenylethylamine was used as a chiral protecting group, while an unexpected Diels-Alder reaction occurred when using a 2-furyl-methyl protection. This rearrangement has been applied to the synthesis of pilolactam, a drug with muscarinic activity. (C) 1999 Elsevier Science Ltd. All rights reserved.
1999
55
5839
5852
The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-allyl-N-benzyl-2,2-dihaloamides to gamma-lactams. Application to the stereoselective synthesis of pilolactam / Ghelfi, Franco; Bellesia, Franco; Forti, Luca; G., Ghirardini; Grandi, Romano; Libertini, Emanuela; M. C., Montemaggi; Pagnoni, Ugo Maria; Pinetti, Adriano; L., De Buyck; A. F., Parson. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 55:(1999), pp. 5839-5852. [10.1016/S0040-4020(99)00247-1]
Ghelfi, Franco; Bellesia, Franco; Forti, Luca; G., Ghirardini; Grandi, Romano; Libertini, Emanuela; M. C., Montemaggi; Pagnoni, Ugo Maria; Pinetti, Ad...espandi
File in questo prodotto:
File Dimensione Formato  
28_T_1999.pdf

Accesso riservato

Tipologia: Versione dell'autore revisionata e accettata per la pubblicazione
Dimensione 701.55 kB
Formato Adobe PDF
701.55 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Licenza Creative Commons
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/611667
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 60
  • ???jsp.display-item.citation.isi??? 65
social impact