胺和羰基化合物縮合得到亞胺,然後通過還原劑(常用的有NaCNBH3,NaBH(OAc)3 等)還原生成相應的胺的反應。
反應機理
首先胺對羰基化合物進行親核加成,脫水生成的亞胺離子。亞胺離子活性中間體被具有親核性的氫負離子進攻,得到胺。反應實例
【Tetrahedron Lett. 1990, 31, 5547–5550】
【J. Org. Chem. 2008, 73, 8829–8837】
【Tetrahedron Lett. 2008, 49, 5211–5213】
參考文獻
1. Borch, R. F., Durst, H. D. J. Am. Chem. Soc. 1969, 91, 3996–3997. Richard F. Borch, born in Cleveland, Ohio, was a professor at the University of Minnesota.
2. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897–2904.
3. Borch, R. F.; Ho, B. C. J. Org. Chem. 1977, 42, 1225–1227.
4. Barney, C. L.; Huber, E. W.; McCarthy, J. R. Tetrahedron Lett. 1990, 31, 5547–5550.
5. Mehta, G.; Prabhakar, C. J. Org. Chem. 1995, 60, 4638–4640.
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8. Lee, O.-Y.; Law, K.-L.; Ho, C.-Y.; Yang, D. J. Org. Chem. 2008, 73, 8829–8837.
9. Sullivan, B.; Hudlicky, T. Tetrahedron Lett. 2008, 49, 5211–5213.
10. Koszelewski, D.; Lavandera, I.; Clay, D.; Guebitz, G. M.; Rozzell, D.; Kroutil, W.Angew. Chem. Int. Ed. 2008, 47, 9337–9340.
編譯自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Borch reductive amination,page 66-67.
相關反應
Leuckart–Wallach反應
酮和胺在過量的甲酸作為還原劑的條件下進行還原胺化的反應。當用醛作為底物的反應為Eschweiler–Clarke還原胺化反應。