Synthesis of new acetal aza-cage compounds via ozonolysis of bis-endo-diol- and diacylnorbornene derivatives |
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| Authors: | Chung-Yi Wu Hui-Chang Lin Hsien-Jen Wu |
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| Institution: | 1. Department of Applied Chemistry, National Chiao Tung University, 1001 Univeristy Rd., Hsinchu, Taiwan, ROC;2. Genomic Research Center, Academia Sinica, 128 Academia Rd., Section 2, Nankang, Taipei, Taiwan, ROC;3. Graduate Institute of Pharmaceutical Chemistry, China Medical University, 91 Hsueh-Shih Rd., Taichung, Taiwan, ROC;4. Department of Environmental Engineering and Health, Yuanpei University, 306 Yuanpei St., Hsinchu, Taiwan, ROC |
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| Abstract: | We synthesized acetal aza-cage compounds directly via ozonolysis of 2,3-bis-endo-diol- and diacylnorbornenes in dichloromethane at ?78 °C. Ozonolysis of the diols followed by addition of amines gave the aza-cage compounds in high yields. The reaction mechanism for the formation of this type of aza-cage compounds is proposed to proceed via the hydroperoxide intermediate. Ozonolysis of the diacetyl norbornene followed by addition of (1) primary amines gave monoaza-cages and diaza-cage, (2) tert-butylamine gave hydroxyl lactone and diaza-cages, and (3) amino acid ester gave optically active aza-cages, in which one compound was converted into chiral aminoalcohol and structure of another was proven by X-ray analysis. A mechanism via the final ozonide and the imine intermediates is proposed for the formation of this type of aza-cages. |
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