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Issue 65, 2014
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Investigation of oxidopyrylium–alkene [5+2] cycloaddition conjugate addition cascade (C3) sequences

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Abstract

Novel oxidopyrylium–alkene [5+2] cycloaddition conjugate addition cascade (C3) sequences are described. Various acetoxypyranone–alkenes with pendant nucleophiles undergo [5+2] cycloaddition followed by conjugate addition from the concave face of the intermediate pyranone toward bridged, tetracyclic ethers. In several cases, 3 new rings, 4 new bonds, and 6 new contiguous stereocenters are constructed with excellent diastereoselectivity. Finally, an asynchronous concerted reaction pathway is proposed to explain the high diastereoselectivity of the oxidopyrylium–alkene [5+2] C3.

Graphical abstract: Investigation of oxidopyrylium–alkene [5+2] cycloaddition conjugate addition cascade (C3) sequences

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Publication details

The article was received on 30 May 2014, accepted on 13 Jun 2014 and first published on 19 Jun 2014


Article type: Communication
DOI: 10.1039/C4CC04163A
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Citation: Chem. Commun., 2014,50, 9130-9133
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    Investigation of oxidopyrylium–alkene [5+2] cycloaddition conjugate addition cascade (C3) sequences

    J. A. Simanis, C. M. Law, E. L. Woodall, C. G. Hamaker, J. R. Goodell and T. A. Mitchell, Chem. Commun., 2014, 50, 9130
    DOI: 10.1039/C4CC04163A

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