1,4-Fragmentatioin of γ-tributylstannyl alcohols by a hypervalent organoiodine compound: a new synthesis of unsaturated carbonyl compounds

Abstract

1,4-Fragmentation of γ-tributylstannyl alcohols using iodosylbenzene, boron trifiluoride–diethyl ether, and dicyclohexycarbodiimide produces unsaturatd carbonyl compounds; the fragmentation, combined with conjugate addition of tributylstannyl-lithium and reduction or alkylation, offers an efficient procedure for the reductive and alkylative ring opening of cyclic vinyl ketones.