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Updated: Aug 21, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A straightforward and versatile synthetic approach to 1-azabicyclic alkaloids
José Barluenga1, Carlos Mateos, Fernando Aznar
1Instituto Universitario de Química Organometálica "Enrique Moles", Unidad asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Spain. barluenga@uniovi.es
Abstract:
A very straightforward route to 1-azabicyclo alkaloid scaffolds with several ring sizes is reported. The final bicyclic structures were built through a synthetic scheme that involved (i) the construction of dienic 4-piperidone systems by an imino-Diels-Alder reaction between aminotrienes and N-omega-vinylimines, in the presence of Yb(OTf)(3), and (ii) the ring-closing metathesis reaction of these cyclic dienes, under the influence of the first-generation Grubbs' Ru-complex catalyst. During this investigations, various polysubstituted azabicyclic ring skeletons, including several examples of the quinolizidine alkaloids, are reported, and their relative stereochemistry is adequately discussed.
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