The first water-soluble C2-symmetric bis(oxazolidinone) 1, a potential bifunctional chiral auxiliary, has been synthesized via regioselective intramolecular cyclization of a biscarbamate. The sodium enolate derived from N,N'-di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high facial selectivity (95:5). Copyright (C) 2000 Elsevier Science Ltd.
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We are grateful to the Korea Institute of Science and Technology for support of this work. We are also grateful to Ms. Jae-Gyung Lee for her assistance in X-ray structure determination.