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Ring opening of 2-acylaziridines by acid chlorides |
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| Authors: | Yongeun Kim Hoseop Yun Won Koo Lee |
| Affiliation: | a Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Kyunggi-Do 449-719, Republic of Korea b Center for Bioactive Molecular Hybrids, Yonsei University, Seoul 120-749, Republic of Korea c Department of Molecular Science and Technology, Ajou University, Suwon 442-749, Republic of Korea d Department of Chemistry and Interdisciplinary Program of Integrated Biotechnology, Sogang University, Seoul 121-742, Republic of Korea |
| Abstract: | Good nucleophilicity of the ring nitrogen in chiral (2R,1′R)-2-acyl-(1′-phenylethyl)aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to yield the β-amino-α-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, and methyl chlorooxoacetate yielded oxazolidin-2-ones, β-amino-α-acetyloxypropionates, and morpholin-2,3-diones, respectively. |
| Keywords: | 2-Acylaziridine Acid chloride Ring opening Morpholin-2,3-dione Isoserine |
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