Stereocontrolled oxazolidinone formation by the addition of 4, 5-disubstituted iminodioxolane to oxirane via a spiro compound

A Baba, K Seki, H Matsuda

Index: Baba, Akio; Seki, Kenji; Matsuda, Haruo Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2684 - 2688

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Citation Number: 6

Abstract

4, 5-Disubstituted 2-imino-1, 3-dioxolanes readily add to oxiranes in the presence of AlC13, furnishing 1, ao~-azolidin-2-ones in a stereospecific manner, where the configurations of oxiranes and iminodioxolanes are reaponsible 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.