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Dipolar Cycloaddition Reactions of Azomethine Ylides Generated by endocyclic‐exocyclic 1,3‐dipole Rearrangement
Author(s) -
Margetić Davor,
Warrener Ronald N.,
Butler Douglas N.,
Holland Craig M.
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2167
Subject(s) - chemistry , azomethine ylide , pyrrolizidine , pyrrolidine , cycloaddition , nitrogen atom , intermolecular force , ring (chemistry) , ylide , 1,3 dipolar cycloaddition , dipole , computational chemistry , medicinal chemistry , stereochemistry , molecule , organic chemistry , catalysis
Dipolar cycloaddition of polycyclic azomethine ylides, in which the central nitrogen atom is part of a pyrrolidine ring and bears a methoxycarbonyl group with norbornenes has been shown to produce two main types of products featuring pyrrolizidine rings. In conjuction with results of quantum chemical calculations (B3LYP), mechanistic rationale was postulated. The key reaction step is unprecedented endocyclic to exocyclic azomethine ylide rearrangement by an intermolecular prototropic migration (formal [1,3] H‐shift).