Synthesis of Heterocyclic Compounds by the Organotin Alkoxide Promoted Cleavage of γ-Bromo β-Lactones

Article abstract of DOI:10.1021/jo00295a044

A variety of 2-oxazolidinones are prepared in good to excellent yields by the organotin alkoxide promoted ring cleavage of γ-bromo β-lactones.This reaction proceeds via the key organotin haloalkoxide intermediate, which reacts with an isocyanate followed by cyclization.Stereoisomerically pure products are obtained by combination with the stereoselective bromolactonization reaction.Moreover, other heterocumulenes such as RN=C=NR, RN=C=S, CO2, and γ-bromo β-lactam are used as substrates.