Efficient Synthesis of Polycyclic γ‐Lactams by Catalytic Carbonylation of Ene‐Imines via Nickelacycle Intermediates. Issue 28 (12th June 2017)

• Record Type: Journal Article
• Authors: Hoshimoto, Yoichi; Ashida, Keita; Sasaoka, Yukari; Kumar, Ravindra; Kamikawa, Ken; Verdaguer, Xavier; Riera, Antoni; Ohashi, Masato; Ogoshi, Sensuke
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 28(2017)
• Page Start: 8206
• Page End: 8210
• Publication Date: 2017-06-12
• Subjects: carbonylation -- cyclization -- enantioselectivity -- heterocycles -- nickel; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201703187
• Languages: English
• ISSNs: 1433-7851

Abstract

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)3 L]. 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. Abstract : 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.