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Robinson annulation

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Name Reactions
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Abstract

Michael addition of cyclohexanones to methyl vinyl ketone followed by intramolecular aldol condensation to afford six-membered α,β-unsaturated ketones.

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References

  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.

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

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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Li, J.J. (2014). Robinson annulation. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_234

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