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.
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