72915-12-9Relevant academic research and scientific papers
Synthesis of N-(2,3,4,5,6-pentafluorobenzyloxy)-γ-lactams by rhodium-catalyzed cyclization of diazo amides
Budny, Marcin,Nowak, Magdalena,Wojtczak, Andrzej,Wolan, Andrzej
, p. 6361 - 6365 (2016/02/18)
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. The rhodium-catalyzed cyclization of diazo amides, derived from O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine, is reported. The reaction leads to a variety of lactams in up to 91 % yield and 88 % ee. The developed method was applied in the synthesis of gabapentin hydrochloride, an important GABA analog.
