Manganese-Mediated Cascade Radical Oxidative Cyclization/1,6-Conjugate Addition of Unsaturated Oximes with p-Quinone Methides: Facile Access to β,β-Diarylmethine Substituted Isoxazolines.

Abstract

A simple and efficient strategy for the synthesis of structurally diverse β,β-diarylmethine substituted isoxazoline derivatives have been developed. This approach employs a manganese-promoted oxidative cyclization coupled with a 1,6-conjugate addition of unsaturated oximes to p-quinone methides. The key features of this study include the formation of C-O and C-C bonds through intramolecular and intermolecular interactions, facilitated by in situ generated iminoxyl radicals. β,β-diarylmethine substituted isoxazolines, bearing a wide range of functional groups, were isolated in high yields.