Generation of spirocyclic quaternary centres via a tandem free radical cyclopropylcarbinyl rearrangement–cyclisation strategy

Abstract

Regio- and stereo-specific construction of spirocyclic quaternary centres may be achieved by hydroxy-directed Simmons–Smith cyclopropanation of an allylic alcohol followed by a tandem free radical cyclopropylcarbinyl rearrangement–cyclisation reaction; generation of the spiro-fused systems is subject to stereoelectronic and kinetic control.