A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates

A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates

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 s...

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Bibliographic Details
Published in:Advanced synthesis & catalysis Vol. 359; no. 18; pp. 3217 - 3225
Main Authors: Beniazza, Redouane, Poittevin, Clément, Lusseau, Jonathan, Massip, Stéphane, Robert, Frédéric, Landais, Yannick
Format: Journal Article
Language:English
Published: Heidelberg Wiley Subscription Services, Inc 18-09-2017
Wiley-VCH Verlag
Subjects:
Alkaloids
Aromatic compounds
Carbamates (tradename)
Chemical Sciences
cyclization
Grignard reagents
Heck reaction
heterocycles
Nitrogen
Organic chemistry
radical reaction
Substrates
Sulfones
vinyl sulfones
Heck reaction
Heterocycle
Grignard
Cyclization
Vinylsulfones
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700485