A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates. Issue 18 (6th September 2017)

• Record Type: Journal Article
• Authors: Beniazza, Redouane; Poittevin, Clément; Lusseau, Jonathan; Massip, Stéphane; Robert, Frédéric; Landais, Yannick
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 18(2017)
• Page Start: 3217
• Page End: 3225
• Publication Date: 2017-09-06
• Subjects: cyclization -- Grignard reagents -- Heck reaction -- heterocycles -- radical reaction -- vinyl sulfones; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700485
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Free‐radical carbo‐alkenylation of N ‐aryl‐, N ‐benzyl‐, and N ‐phenethyl‐ene‐carbamates with a disulfone provides vinyl sulfones which may then be functionalized and engaged in Heck‐type coupling to furnish highly substituted 5‐, 6‐ and 7‐membered nitrogen heterocycles. Grignard‐mediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the Aspidosperma family. Abstract :