Construction of atropisomeric benzoxepinone-embedded styrenes via intramolecular [3+2] cycloaddition and catalytic kinetic resolution

Abstract

We present an intramolecular [3+2] cycloaddition of innovative (E)-α-aryl enal derivatives with 4-aminopyrazolone hydrochlorides/3-aminooxindole hydrochlorides to afford an array of atropisomeric benzoxepinone-based styrenes fused to spiro[pyrrolidine–pyrazolone/oxindole] scaffolds, and kinetic resolutions of the racemic adducts were implemented by reacting with benzyl alcohols, giving the corresponding two types of axially chiral styrenes in enantioenriched form with high s-factor. In addition, product transformations such as oxidative dehydrogenation and cross-coupling reactions have been demonstrated.