Synthesis of the first water-soluble C2-symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary |
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| Institution: | 1. School of Materials Science and Engineering, Nanchang University, Nanchang, Jiangxi 330031, China;2. Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China;3. Department of Chemistry and the Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, China;4. Department of Chemistry and Center for Nanotechnology and Institute of Biomedical Technology, Chung-Yuan Christian University, Chung-Li 32023, Taiwan, ROC |
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| Abstract: | 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). |
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