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Org Lett. 2011 May 6;13(9):2220-3. doi: 10.1021/ol200471w. Epub 2011 Apr 1.

Iodobenzene-catalyzed intramolecular oxidative cyclization reactions of δ-alkynyl β-ketoesters.

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  • 1Department of Chemical & Biological Sciences, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK.


Iodobenzene is shown to catalyze the 5-exo-dig cyclization of δ-alkynyl β-ketoesters under oxidative conditions that generate hypervalent iodine species in situ. The cyclopentane products contain adjacent quaternary and tertiary stereocenters which are generated with excellent diastereoselectivity.

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