Stereoconservative Formation and Reactivity of α-Chalcogen-Functionalized Vinyllithium Compounds from α-Bromo-vinylic Chalcogenides

Abstract

Bromine/lithium exchange was performed upon treatment of α-bromo-vinylic chalcogenides with butyllithium in hexane at room temperature to provide α-chalcogen-vinyllithium intermediates quantitatively. Addition of electrophiles to the lithiated compounds gave the corresponding functionalized vinylic chalcogenides in good yields with retention of configuration.