Synthesis of carbocycles from ω-substituted α,β-unsaturated esters via radical-induced cyclizations

Abstract

The intramolecular radical cyclization of ω-bromo α,β-unsaturated esters for the synthesis of carbocyclic compounds is described. The effect of carbon chain substituents, the bulk of the ester group, and the olefin geometry were examined. The highest level of stereoselectivity (trans/cis: 9/1) was achieved with the Z ester via an exo cyclization. The sequential radical cyclization of a dihalodienoate to give a cis-fused bicyclic structure is also described.