Benzoin缩合和Retro-Benzoin缩合

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   在氰根离子存在下，芳香醛或乙二醛反应生成安息香（α-羟基酮或偶姻），这个反应称为Benzoin缩合。其相反过程叫做Retro-Benzoin缩合，通常用来合成酮。在这个缩合反应中，一分子醛基加成到另个醛基的C=O基团，其中有一个醛作为给予体，另一个醛作为接受体。一些醛只能作为给予体或者接受体，所以它们不能够自身缩合，而当一些醛具有两个功能时就能发生自身缩合。在弱碱条件下某些噻唑盐也可以催化该反应，且这类Benzoin缩合比传统的缩合更加有利于合成，因为它可以使烯醇类醛和非烯醇类醛反应，并且可以使用不对称催化剂。




反应机理


氰离子催化的Benzoin缩合的所有步骤完全可逆




噻唑盐催化的Benzoin缩合




反应实例





参考文献


1. Lapworth, A. J. J. Chem. Soc. 1903, 995.

2. Lapworth, A. J. J. Chem. Soc. 1904, 1206-1215.

3. Staudinger, H. Ber. Dtsch. Chem. Ges. 1913, 46, 3535-3538.

4. Ide, W. S., Buck, J. S. Org. React. 1948, 4, 269-304.

5. Pohl, M., Lingen, B., Muller, M. Chemistry—A European Journal 2002, 8, 5288-5295.

6. Suzuki, Y., Takemura, Y., Iwamoto, K.-i., Higashino, T., Miyashita, A. Chem. Pharm. Bull. 1998, 46, 199-206.

7. Barta, T. E., Stealey, M. A., Collins, P. W., Weier, R. M. Bioorg. Med. Chem. Lett. 1998, 8, 3443-3448.


本文来自  Name Reactions:A Collection of Detailed Mechanisms

and Synthetic Applications--Fifth Edition，有机人名反应——机理及应用 第四版


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