Diastereoselective Synthesis of 1,2-Dihydrobenzofuro[3,2-<i>b</i>]pyridines via a Carbon–Carbon Double-Bond Cleavage/Rearrangement Cascade
Chi‐Fan Zhu, Ling-Qi Chen, Wen‐Juan Hao, Chen‐Chang Cui, Shu‐Jiang Tu, Bo Jiang
Abstract
A new Lewis acid-catalyzed [2 + 2] cycloaddition/retroelectrocyclization (CA-RE)/1,6-addition relay of aurone-derived 1-azadienes and 1-alkynylnaphthalen-2-ols has been reported, leading to the regio- and diastereoselective synthesis of 1,2-dihydrobenzofuro[3,2-b]pyridine with a chiral carbon center and an axial chirality in good yields. This protocol enables the C–C double-bond scission/recombination to rapidly construct aza-heterocyclic architectures and features 100% atom utilization, a wide substrate scope, good compatibility with substituents, and excellent diastereoselectivity.
Topics & Concepts
ChemistryDouble bondBond cleavageCycloadditionStereochemistryPyridineCleavage (geology)CascadeTriple bondLewis acids and basesCombinatorial chemistryMedicinal chemistryCatalysisOrganic chemistryGeotechnical engineeringChromatographyEngineeringFracture (geology)Cyclopropane Reaction MechanismsSynthesis of Organic CompoundsCatalytic C–H Functionalization Methods