Aza-Cope重排(氮杂科甫重排)指在重排分子中含亚胺离子结构单元的氮杂-[3,3]-σ迁移重排,生成产物为胺的衍生物。
反应机理
氮杂科甫重排的起因是Mannich反应,先形成亚胺离子继而引发科甫重排。一般而言,氧杂及氮杂科甫重排比纯碳链的科甫重排温度要低,反应要快。
反应实例
参考文献
1. Oehlschlager, A. C., Zalkow, L. H. Bridged ring compounds. X. J. Org. Chem. 1965, 30, 4205-4211.
2. Hill, R. K., Gilman, N. W. Tetrahedron Lett. 1967, 1421-1423.
3. Lipkowitz, K. B., Scarpone, S., McCullough, D., Barney, C. Tetrahedron Lett. 1979, 2241-2244.
4. Brummond, K. M., Lu, J. Org. Lett. 2001, 3, 1347-1349.
5. Bennett, D. J., Hamilton, N. M. Tetrahedron Lett. 2000, 41, 7961-7964.
6. Madin, A., O'Donnell, C. J., Oh, T., Old, D. W., Overman, L. E., Sharpe, M. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 2934-2936.
7. Knight, S. D., Overman, L. E., Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776-5788.
摘自:有机人名反应——机理及应用 第四版,Strategic Applications of Named Reactions in Organic Synthesis
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