Efficient Synthesis of Polycyclic γ‐Lactams by Catalytic Carbonylation of Ene‐Imines via Nickelacycle Intermediates. (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. Volume 129:Number 28(2017)
• Page Start: 8318
• Page End: 8322
• Publication Date: 2017-06-12
• Subjects: Carbonylierungen -- Cyclisierungen -- Enantioselektivität -- Heterocyclen -- Nickel; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201703187
• Languages: English
• ISSNs: 0044-8249

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.