Blue Light-Promoted Formal [4+1]-Annulation of Diazoacetates with <i>o</i>-Aminoacetophenones: Synthesis of Polysubstituted Indolines and Computational Study
Jinzhou Chen, Shuhao Liu, Xinxin Lv, Kemiao Hong, Jinping Lei, Xinfang Xu, Wenhao Hu
Abstract
A blue light-promoted formal [4+1]-annulation of diazoacetates with o-aminoacetophenones has been reported, which provides an environmentally friendly method for the synthesis of polysubstituted indoline derivatives in moderate to good yields with excellent diastereoselectivities. Detailed mechanistic studies through density functional theory calculations reveal that the (E)-enol species is the key intermediate in this transformation, and the excellent diastereoselectivity is enabled via H-bonding in the intramolecular Aldol-type addition.
Topics & Concepts
AnnulationChemistryIntramolecular forceIndolineEnolDensity functional theoryAldol condensationCombinatorial chemistryComputational chemistryStereochemistryOrganic chemistryCatalysisCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions