Lewis acid-catalyzed (3 + 2) annulation of bicyclobutanes with ynamides: access to 2-amino-bicyclo[2.1.1]hexenes
Deeptanu Sarkar, Shiksha Deswal, Rohan Chandra Das, Akkattu T. Biju
Abstract
nucleophilic addition facilitated by the nitrogen lone pair from the alkynyl group of the ynamides to the unsubstituted side of the BCBs, followed by the annulation of the resulting enolate with the keteniminium species. For the first time, the C-C triple bond of ynamides was utilized as the coupling partner for BCBs, resulting in products adorned with a functionalizable amino group and an integrated strained alkene moiety.
Topics & Concepts
Bicyclic moleculeAnnulationCatalysisChemistryLewis acids and basesStereochemistryStrain (injury)Medicinal chemistryCombinatorial chemistryOrganic chemistryBiologyAnatomyCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods