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Reductive coupling of N-methoxycarbonyl lactams with benzophenone and 9-fluorenone by low-valent titanium
Authors:Naoki Kise  Yosei Takenaga  Yohei Ishikawa  Yoichi Morikami  Toshihiko Sakurai
Affiliation:Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan
Abstract:The reductive coupling of N-methoxycarbonyl lactams with benzophenone by Zn-TiCl4 in THF gave cross-coupled products as cyclic α-diphenylidene-N-methoxycarbonylamines and ring-opening α,α-diphenyl-α-hydroxy-ω-(N-methoxycarbonyl)amino ketones selectively depending on the reduction conditions. The reductive coupling of N-methoxycarbonyl lactams with 9-fluorenone by Zn-TiCl4 gave cyclic α-(9H-fluoren-9-ylidene)-N-methoxycarbonylamines preferentially irrespective to the conditions.
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