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Functionalization of Cmath image[BOND]H and Cmath image[BOND]H Bonds: Synthesis of Spiroindenes by Enolate-Directed Ruthenium-Catalyzed Oxidative Annulation of Alkynes with 2-Aryl-1,3-dicarbonyl Compounds

Authors


  • We thank the European Commission (Marie Curie International Incoming Fellowship to S.R.C., Project No. PIIF-GA-2009-252561) and the University of Edinburgh for financial support. We are grateful to the EPSRC for a Leadership Fellowship to H.W.L. We thank Martin D. Wieczysty (University of Edinburgh) for assistance in the preparation of substrates, and Gary S. Nichol (University of Edinburgh) for X-ray crystallography. The EPSRC National Mass Spectrometry Service Centre is gratefully acknowledged for providing high-resolution mass spectra.

Abstract

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Ru(de) awakening: The synthesis of carbocycles by the ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl cyclic 1,3-dicarbonyl substrates is described. Proceeding by the functionalization of Cmath image[BOND]H and Cmath image[BOND]H bonds, and the formation of an all-carbon quaternary center, the reaction provides a diverse range of spiroindenes in good yields with high levels of regioselectivity.

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