231606-11-4Relevant academic research and scientific papers
The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-allyl-N-benzyl-2,2-dihaloamides to γ-lactams. Application to the stereoselective synthesis of pilolactam
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.
, p. 5839 - 5852 (1999)
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.
Efficient and green route to γ-lactams by copper-catalysed reversed atom transfer radical cyclisation of α-polychloro-N-allylamides, using a low load of metal (0.5 mol%)
Bellesia, Franco,Clark, Andrew J.,Felluga, Fulvia,Gennaro, Armando,Isse, Abdirisak A.,Roncaglia, Fabrizio,Ghelfi, Franco
, p. 1649 - 1660 (2013)
The cyclisation of N-allyl-N-substituted-α-polychloroamides is efficiently obtained through a copper-catalysed activators regenerated by electron transfer-atom transfer radical cyclisation process, with a metal load of only 0.5 mol%. The redox catalyst is
