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Robinson关环反应2020-02-12

环己酮先对甲基烯基酮进行迈克尔加成,然后进行分子内的羟醛缩合关环得到六元环的α,β-不饱和酮的反应。

反应机理

反应实例




成环戊烯环的Robinson反应

参考文献

1. Rapson, W. S.; Robinson, R. J. Chem. Soc. 1935, 1285–1288. Robert Robinson used the Robinson annulaton in his total synthesis of cholesterol. Here is a story told by Derek Barton about Robinson and Woodward: “By pure chance, the two great men met early in a Monday morning on an Oxford train station platform in 1951. Robinson politely asked Woodward what kind of research he was doing these days; Woodward replied that he thought that Robinson would be interested in his recent total synthesis of cholesterol. Robinson, incensed and shouting ‘Why do you always steal my research topic?’, hit Woodward with his umbrella.”—An excerpt from Barton, Derek, H. R. Some Recollections of Gap Jumping, American Chemical Society, Washington, D.C., 1991.【Robert Robinson 在全合成胆固醇(cholesterol)的过程中利用Robert关环反应 。Derek Barton曾讲过一个有关Robinson和Woodward的小故事:“1951年一个星期一的早晨,一个偶然的机会,两个著名的科学家在牛津火车站的月台上偶遇。Robinson很礼貌的问Woodward最近在做哪方面的研究。Woodward回答道,Robinson应该对最近他的cholesterol的全合成有兴趣。Robinson愤怒的大喊道,‘为什么你总是偷我的研究课题?’并抄起伞向Woodward抡去。”—-摘自Barton, Derek, H. R.的《Some Recollections of Gap Jumping, American Chemical Society, Washington, D.C., 1991.》】

2. Gawley, R. E. Synthesis 1976, 777–794. (Review).

3. Guarna, A.; Lombardi, E.; Machetti, F.; Occhiato, E. G.; Scarpi, D. J. Org. Chem. 2000, 65, 8093–8096.

4. Tai, C.-L.; Ly, T. W.; Wu, J.-D.; Shia, K.-S.; Liu, H.-J. Synlett 2001, 214–217.

5. Jung, M. E.; Piizzi, G. Org. Lett. 2003, 5, 137–140.

6. Singletary, J. A.; Lam, H.; Dudley, G. B. J. Org. Chem. 2005, 70, 739–741.

7. Yun, H.; Danishefsky, S. J. Tetrahedron Lett. 2005, 46, 3879–3882.

8. Jung, M. E.; Maderna, A. Tetrahedron Lett. 2005, 46, 5057–5061.

9. Zhang, Y.; Christoffers, J. Synthesis 2007, 3061–3067.

10. Jahnke, A.; Burschka, C.; Tacke, R.; Kraft, P. Synthesis 2009, 62–68.

11. Bradshaw, B.; Parra, C.; Bonjoch, J. Org. Lett. 2013, 15, 2458–2461.

编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Robinson annulation,page 519-520.

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