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.
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 / Ghelfi, Franco; Af, Parsons; D., Tommasini; Mucci, Adele. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2001:10(2001), pp. 1845-1852. [10.1002/1099-0690(200105)2001:10<1845::AID-EJOC1845>3.0.CO;2-I]
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
GHELFI, Franco;MUCCI, Adele
2001
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.
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