Stereocontrolled Oxazolidinone Formation by the Addition of 4,5-Disubstituted Iminodioxolane to Oxirane via a Spiro Compound

Article abstract of DOI:10.1021/jo00008a021

4,5-Disubstituted 2-imino-1,3-dioxolanes readily add to oxiranes in the presence of AlCl3, furnishing 1,3-oxazolidin-2-ones in a stereospecific manner, where the configurations of oxiranes and iminodioxolanes are responsible for the configuration of products and the feasibility of the addition, respectively.A preliminary adduct, a spiro compound intermediate, is isolated, and its decomposition to oxazolidinone is demonstrated.