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- Title
Synthesis of N-(2,3,4,5,6-Pentafluorobenzyloxy)-γ-lactams by Rhodium-Catalyzed Cyclization of Diazo Amides.
- Authors
Budny, Marcin; Nowak, Magdalena; Wojtczak, Andrzej; Wolan, Andrzej
- Abstract
Rhodium-catalyzed cyclization of N-(2,3,4,5,6-pentafluoro-benzyloxy) diazo amides leading to the corresponding γ-lactams is described. The cyclization is based on the intramolecular catalytic insertion into the C--H bond. Fourteen lactams were obtained with up to 91% yield and 88% ee. Gabapentin hydrochloride, a GABA analog, was also synthesized by this method, which shows that deprotection of the 2,3,4,5,6-pentafluorobenzyloxy group is possible.
- Subjects
DIAZO compounds; RING formation (Chemistry); LACTAMS; CHEMICAL synthesis; CATALYSTS
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 29, p6361
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402571