Marcin Budny - Synthesis of N-(2,3,4,5,6-Pentafluorobenzyloxy)-γ-lactams by Rhodium-Catalyzed Cyclization of Diazo Amides

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      Publication Details (including relevant citation   information):

      Marcin Budny, Magdalena Nowak, Andrzej Wojtczak, Andrzej Wolan,   Eur. J. Org. Chem., 2014, Early View. doi: 10.1002/ejoc.201402571

      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.

      Address (URL): http://dx.doi.org/10.1002/ejoc.201402571