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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
Author(s) -
Ghelfi Franco,
Parsons Andrew F.,
Tommasini Daniele,
Mucci Adele
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1845::aid-ejoc1845>3.0.co;2-i
Subject(s) - cycloaddition , chemistry , pyrrolizidine , intramolecular force , amide , diels–alder reaction , ring (chemistry) , electronegativity , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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.