Premium
Synthesis of N ‐(2,3,4,5,6‐Pentafluorobenzyloxy)‐γ‐lactams by Rhodium‐Catalyzed Cyclization of Diazo Amides
Author(s) -
Budny Marcin,
Nowak Magdalena,
Wojtczak Andrzej,
Wolan Andrzej
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402571
Subject(s) - chemistry , diazo , rhodium , catalysis , yield (engineering) , intramolecular force , medicinal chemistry , lactam , hydrochloride , stereochemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
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.