Dipolar Cycloaddition Reactions of Azomethine Ylides Generated by endocyclic‐exocyclic 1,3‐dipole Rearrangement |
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| Authors: | Davor Margeti? Ronald N Warrener Douglas N Butler Craig M Holland |
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| Institution: | 1. Laboratory for Physical‐Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ru?er Bo?kovi? Institute, Zagreb, Croatia;2. Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, Australia |
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| Abstract: | 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). |
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