Copper(I)‐Catalyzed Highly Enantioselective [3+3]‐Cycloaddition of β‐Aryl/Alkyl Vinyl Diazoacetates with Nitrones
Haifeng Zheng, Isa Faghihi, Michael P. Doyle
Abstract
Abstract β‐Aryl/alkyl vinyl diazoacetates were investigated in metallo‐vinylcarbene reactions with nitrones, revealing a Rh 2 (OAc) 4 ‐catalyzed cyclopropene dimerization reaction and a copper(I) catalyzed [3+3]‐cycloaddition of nitrones. The chiral cyclopropyl‐In‐SaBox ligand with copper(I) catalysis could realize the asymmetric version of the cycloaddition reaction, delivering various 3,6‐dihydro‐1,2‐oxazine derivatives in good yield and with excellent enantioselectivity under mild conditions.
Topics & Concepts
ChemistryCycloadditionCatalysisArylEnantioselective synthesisAlkylYield (engineering)CopperCyclopropeneMedicinal chemistryLigand (biochemistry)Organic chemistryCombinatorial chemistryBiochemistryReceptorMetallurgyMaterials scienceCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions