Intramolecular Cycloaddition of 1,3-Enynes with Alkenes

By: Josephine Nakhla, ChemFiles Volume 10 Article 4

Echavarren and co-workers employed a crystalline gold complex containing either the o-biphenyl phosphine ligand JohnPhos, or a bulky aryl ether phosphine under mild conditions to eff ect the [4+2] cycloaddition of 1,3-enynes with olefi ns. A family of biand tricyclic scaff olds were prepared in good yields (Scheme 2). Both electron-withdrawing and electron-donating groups were tolerated on the aryl moiety.

Scheme 2 Intramolecular cycloaddition of 1,3-enynes with alkenes

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References

  1. Nieto-Oberhuber, C.; Pèrez-Galán, P.; Herrero-Gómez, E.; Lauterbach, T.; Rodriguez, C.; López, S.; Bour, C.; Rosellón, A.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269.

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