Wittig

本反应也被称为Wittig反应Schlosser改进法,常规的Wittig反应中叶立德和醛反应得到是Z构型的烯烃,而此反应生成的是E构型的烯烃。

反应机理

在此反应的条件下赤式(erythreo)的甜菜碱类似物转化为苏式(threo)的甜菜碱类似物。

反应实例

参考文献

1. (a) Schlosser, M.; Christmann, K. F. Angew. Chem. Int. Ed. 1966, 5, 126. (b) Schlosser,

M.; Christmann, K. F. Ann. 1967, 708, 1􀀐-35. (c) Schlosser, M.; Christmann, K. F.;

Piskala, A.; Coffinet, D. Synthesis 1971, 29􀀐-31. Born in Ludwigshafen on Rhine

(Germany), Manfred Schlosser earned his Ph.D. in 1960 under Georg Wittig. He intiailly worked at at the German Cancer Research Center and moved to France to be a professor at the University of Lausanne. Schlosser retired in 2004.(Manfred Schlosser生于德国莱茵河畔的路德维希港,1960年在Georg Wittig指导下获得Ph.D.学位。开始在德国肿瘤研究中心工作,后来又去法国任洛桑大学教授,2004年退休。)

2. van Tamelen, E. E.; Leiden, T. M. J. Am. Chem. Soc. 1982, 104, 2061-􀀐2062.

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4. Sarkar, T. K.; Ghosh, S. K.; Rao, P. S.; Satapathi, T. K.; Mamdapur, V. R. Tetrahedron1992, 48, 6897-􀀐6908.

5. Deagostino, A.; Prandi, C.; Tonachini, G.; Venturello, P. Trends Org. Chem. 1995, 5,103􀀐-113. (Review).

6. Celatka, C. A.; Liu, P.; Panek, J. S. Tetrahedron Lett. 1997, 38, 5449􀀐-5452.

7. Panek, J. S.; Liu, P. J. Am. Chem. Soc. 2000, 122 11090􀀐-11097.

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9. Kraft, P.; Popaj, K. Eur. J. Org. Chem. 2004, 4995-􀀐5002.

10. Kraft, P.; Popaj, K. Eur. J. Org. Chem. 2008, 4806􀀐-4814.

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12. Mikula, H.; Hametner, C.; Froehlich, J. Synth. Commun. 2013, 43, 1939􀀐-1946.

编译自:J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Schlosser modification of the Wittig reaction,page 634-635.

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