Tetrahedron p. 5839 - 5852 (1999)
Update date:2022-08-05
Topics:
Ghelfi, Franco
Bellesia, Franco
Forti, Luca
Ghirardini, Gianluca
Grandi, Romano
Libertini, Emanuela
Montemaggi, Maria C.
Pagnoni, Ugo M.
Pinetti, Adriano
De Buyck, Laurent
Parsons, Andrew F.
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 γ-lactams. An appreciable chiral induction was observed at the C-4 site when α-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.
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Doi:10.1080/15257779908041531
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(1980)Doi:10.1021/ja016525o
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