Weiss–Cook缩合反应

3-羰基戊二酸酯和邻二羰基化合物在缓冲溶液中缩合得到顺式-双环[3.3.0]辛烷-3,7-二酮（cis-bicyclo[3.3.0]octane-3,7-dione）的反应。产物极易脱羧。

反应机理

一分子的3-羰基戊二酸酯先和邻二羰基化合物缩合生成环戊二烯酮，接着与另一分子的3-羰基戊二酸酯经过两次迈克尔加成得到产物。

反应实例

参考文献

1. Weiss, U.; Edwards, J. M. Tetrahedron Lett. 1968, 9, 4885–4887. Weiss was a scientist at the National Institutte of Health in Bethesda, Maryland.

2. Bertz, S. H.; Cook, J. M.; Gawish, A.; Weiss, U. Orga. Synth. 1986, 64, 27–38. James M. Cook is a professor at University of Wisconsin, Milwaukee.

3. Kubiak, G.; Fu, X.; Gupta, A. K.; Cook, J. M. Tetrahedron Lett. 1990, 31, 4285–4288.

4. Wrobel, J.; Takahashi, K.; Honkan, V.; Lannoye, G.; Bertz, S. H.; Cook, J. M. J. Org Chem. 1983, 48, 139–141.

5. Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 47, 3665–3710.

6. Paquette, L. A.; Kesselmayer, M. A.; Underiner, G. E.; House, S. D.; Rogers, R. D.; Meerholz, K.; Heinze, J. J. Am. Chem. Soc. 1992, 114, 2644–2652.

7. Fu, X.; Cook, J. M. Aldrichimica Acta 1992, 25, 43–54. (Review).

8. Fu, X.; Kubiak, G.; Zhang, W.; Han, W.; Gupta, A. K.; Cook, J. M. Tetrahedron 1993, 49, 1511–1518.

9. Williams, R. V.; Gadgil, V. R.; Vij, As.; Cook, J. M.; Kubiak, G.; Huang, Q. J. Chem. Soc., Perkin Trans. 1 1997, 1425–1428.

10. van Ornum, S. G.; Li, J.; Kubiak, G. G.; Cook, J. M. J. Chem. Soc., Perkin Trans. 1. 1997, 3471–3478.

11. Galatsis, P. Weiss–Cook Reaction, In Name Reactions for Carbocyclic Ring Formations, Li, J. J., Ed.; Wiley: Hoboken, NJ, 2010, pp 181–196. (Review).

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Weiss–Cook condensation，page 624-625.