Trapping of radical intermediate in reaction of sulphonates with sodium iodide/zinc/dme. Total frontier orbital control of stereoselectivity in ring closure.

Abstract Reductive cyclization has been shown to accompany reduction on NaI/Zn/DME treatment of sulphonates of γ,δ- unsaturated alcohols. Stereoselectivity is due to FMO control with axial extension of SOMO of cyclohexyl radical playing a crucial role.