139669-61-7Relevant 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 (2007/10/03)
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 Synthesis of 2-Vinyl-γ-butyrolactones and 2-Vinyl-γ-butyrolactams by Palladium-Catalyzed Decarboxylative Carbonylation
Bando, Takashi,Tanaka, Shuji,Fugami, Keigo,Yoshida, Zen-ichi,Tamaru, Yoshinao
, p. 97 - 110 (2007/10/02)
4-Vinyl-1,3-dioxan-2-ones (cyclic carbonates) undergo decarboxylation-carbonylation by the catalysis of Pd(0) species under CO (in most cases, 1 atm) to provide 2-vinyl-γ-butyrolactones in good yields.The course of the reaction of 6-vinyltetrahydro-2H-1,3
