3 years ago

Efficient Synthesis of Polycyclic γ-Lactams by Catalytic Carbonylation of Ene-Imines via Nickelacycle Intermediates

Efficient Synthesis of Polycyclic γ-Lactams by Catalytic Carbonylation of Ene-Imines via Nickelacycle Intermediates
Yukari Sasaoka, Ravindra Kumar, Sensuke Ogoshi, Yoichi Hoshimoto, Masato Ohashi, Antoni Riera, Xavier Verdaguer, Ken Kamikawa, Keita Ashida
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. CO gas is employed in a nickel(0)-catalyzed [2+2+1] carbonylative cycloaddition reaction with 1,5- and 1,6-ene-imine substrates. The method affords a variety of tri- and tetracyclic γ-lactams in excellent yields with 100 % atom efficiency.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703187

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