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Intramolecular Diels-Alder cycloaddition of N-allyl-N-(2-furylmethyl)amides - First step of a new route towards the synthesis of a densely functionalized pyrrolizidine ring

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Publication details

JournalEuropean Journal of Organic Chemistry
DatePublished - May 2001
Issue number10
Number of pages8
Pages (from-to)1845-1852
Original languageEnglish

Abstract

The intramolecular Diels-Alder reaction of N-allyl-N-(2-furylmethyl)amides to exo-N-acyl-3-aza-10-oxatricyclo[5.2.1.0(1)-,5]dec-8-enes is described. The cycloaddition is controlled not only by the size of the amide appendage, but, also by electronegativity of the amide. An example of a new approach towards the synthesis of a highly functionalized pyrrolizidine ring, which links this Diels-Alder cycloaddition to an halogen atom transfer radical cyclization, is reported.

    Research areas

  • amides, Diels-Alder reactions, polycyclic aliphatic compounds, pyrrolizidines, radicals, radical reactions, TRICYCLIC NITROGEN-HETEROCYCLES, RADICAL CYCLIZATION, GAMMA-LACTAMS, FURAN DIENE, ORGANOMETALLIC REAGENTS, CONSTRUCTION, IMDAF, REARRANGEMENT, SUBSTITUENTS, DERIVATIVES

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