Rare Gold-Catalyzed 4-<i>exo</i>-<i>dig</i> Cyclization for Ring Expansion of Propargylic Aziridines toward Stereoselective (<i>Z</i>)-Alkylidene Azetidines, via Diborylalkyl Homopropargyl Amines
Oriol Salvadó, Jorge Pérez‐Ruíz, Alba Mesas, M. Mar Díaz‐Requejo, Pedro J. Pérez, Elena Fernández
Abstract
High Resolution Image Download MS PowerPoint Slide We report an uncommon 4- exo - dig cyclization of N -tosyl homopropargyl amines, catalyzed by [AuCl(PEt 3 )]/AgOTf, to prepare stereoselective ( Z )-2-alkylidene-1-tosylazetidine compounds. The reaction outcome contrasts with the gold-catalyzed cyclization of N -tosyl homopropargyl amines containing a methyl group at the propargylic position that provides substituted 2,3-dihydropyrroles via a 5- endo - dig mechanism. The access to N -tosyl homopropargyl amines is possible by the regioselective nucleophilic attack of α-diboryl alkylidene lithium salts to propargylic aziridines.
Topics & Concepts
StereoselectivityChemistryDigRing (chemistry)CatalysisCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryComputer scienceWorld Wide WebCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsCatalytic C–H Functionalization Methods