Rh-catalyzed intramolecular debenzylative cyclization of amines. Butyrolactams from benzylamines having a chloroacetylene moiety

Iridium-Catalyzed Single-Step N-Substituted Lactam Synthesis from Lactones and Amines

“…1 H NMR (499 MHz, CDCl 3 ): δ 7.31 (d, J = 8.3 Hz, 2H), 7.19 (d, J = 8.8 Hz, 2H), 4.43 (s, 2H), 3.26 (t, J = 7.2 Hz, 2H), 2.45 (t, J = 8.3 Hz, 2H), 2.01 (quin, J = 7.6 Hz, 2H). The spectral data were consistent with those reported in the literature …”

“…The spectral data were consistent with those reported in the literature. 22 1-[(4-Trifluoromethylphenyl)methyl]-2-pyrrolidinone (3ae). Yellow liquid (105 mg, 86%).…”

Late Transition Metal-Catalyzed Hydroamination and Hydroamidation

“…818 In 2011, the Urabe group reported an efficient synthesis of butyrolactones via Rh-catalyzed intramolecular debenzylative hydroamination of molecules bearing both a benzylamino and a chloroacetylene moiety (Scheme 287). 819 It was suggested that the rhodium catalyst promotes the intramolecular aminometalation to give the benzylammonium salt intermediate, which is attacked by water to cleave the benzylic C−N bond. Hydrolysis of chlorovinyl rhodium intermediate affords the lactam.…”