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Efficient Synthesis of Polycyclic γ-Lactams by Catalytic Carbonylation of Ene-Imines via Nickelacycle Intermediates |
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| Authors: | Dr Yoichi Hoshimoto Keita Ashida Yukari Sasaoka Dr Ravindra Kumar Prof?Dr Ken Kamikawa Prof?Dr Xavier Verdaguer Prof?Dr Antoni Riera Prof?Dr Masato Ohashi Prof?Dr Sensuke Ogoshi |
| Institution: | 1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, 565-0871 Japan;2. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka, 599-8531 Japan;3. Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Barcelona, 08028 Spain
Departament de Química Inorgànica i Orgànica, Secció Orgànica, Universitat de Barcelona, Barcelona, 08028 Spain |
| Abstract: | The nickel(0)-catalyzed carbonylative cycloaddition of 1,5- and 1,6-ene-imines with carbon monoxide (CO) is reported. Key to this reaction is the efficient regeneration of the catalytically active nickel(0) species from nickel carbonyl complexes such as Ni(CO)3L]. A variety of tri- and tetracyclic γ-lactams were thus prepared in excellent yields with 100 % atom efficiency. Preliminary results on asymmetric derivatives promise potential in the synthesis of enantioenriched polycyclic γ-lactams. |
| Keywords: | carbonylation cyclization enantioselectivity heterocycles nickel |