Radical hydrogen abstraction–cyclization with a 2-bromovinylsilyl group as a bifunctional tether

In order to develop an efficient method for the regio- and stereoselective introduction of a carbon substituent, a radical hydrogen abstraction–cyclization using 1- and 2-bromovinylsilyl groups as bifunctional tethers was studied. Although, the selective introduction of a carbon substituent at the position β to the hydroxyl was unsuccessful, a carbon substituent was introduced with the 2-bromovinylsilyl ethers via a hydrogen abstraction–cyclization. These reactions were analyzed based on the bond dissociation energies obtained by theoretical calculations.