Skeletal Editing of Isoindolines to Tetralins

Abstract

We present a skeletal editing strategy for transforming isoindolines into tetralins via a cascade N-atom removal deconstruction followed by a Diels-Alder reaction between in situ generated o-quinodimethanes and activated alkenes. This approach features a broad substrate scope, excellent stereoselectivity, and high yields, demonstrating its applicability to complex bioactive compounds and natural products. Notably, case studies showcase the efficient construction of challenging spirocyclic and bridged systems, underscoring the method's versatility and potential for advancing applications in synthetic chemistry.