Nitrogen-interrupted <i>halo</i>-Prins/<i>halo</i>-Nazarov fragment coupling cascade for the synthesis of indolines
Aleksa Milosavljevic, Connor Holt, Alison J. Frontier
Abstract
-Prins reaction of ketones, thus enabling the formation of quaternary stereocenters. Additionally, we describe the outcomes of secondary alcohol enyne couplings, which exhibit helical chirality transfer. Furthermore, we investigate the impact of aniline enyne substituents on the reaction and evaluate the tolerance of different functional groups. Finally, we discuss the reaction mechanism and demonstrate various transformations of the prepared indoline scaffolds, highlighting their applicability in drug discovery campaigns.
Topics & Concepts
HaloCascadeFragment (logic)ChemistryCoupling (piping)NitrogenStereochemistryPhysicsComputer scienceAstrophysicsOrganic chemistryMaterials scienceProgramming languageGalaxyMetallurgyChromatographyCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsCyclopropane Reaction Mechanisms