Radical cyclization of α-iodo enones by photoinduced electron transfer reaction

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Chin-Kang Sha


Abstract

A facile intramolecular radical cyclization of α-iodo enones effected by triethylamine-mediated photoinduced electron transfer (PET) reactions is described.


References

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  8. Enones 7 and 10 were synthesized by the reaction of 3-ethoxycyclohex-2-en-1-one with 4-trimethylsilylbut-3-ynylmagnesium bromide or hex-3-ynylmagnesium bromide followed by acid hydrolysis: D. Becker, Z. Harel, M. Nagler and A. Gillon, J. Org. Chem., 1982, 47, 449 Search PubMed Compounds 13, 16, 19, 22 and 25 were prepared by condensation of 3-trimethylsilylprop-2-yn-1-ol or prop-2-yn-1-ol or 3-trimethylsilylprop-2-ynylamine with cyclohexane-1,3-dione or cyclopentane-1, 3-dione.
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  10. Compound 31 was prepared from 2-iodocyclohex-2-enone by reduction with sodium borohydride–cerium chloride followed by treatment with sodium hydride and prop-2-ynyl bromide. Compound 33 was obtained by reduction of 8 using sodium borohydride–cerium chloride followed by treatment with sodium hydride and iodomethane.
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