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Multicomponent Cycloadditions:  The Four-Component [5+1+2+1] Cycloaddition of Vinylcyclopropanes, Alkynes, and CO

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    Multicomponent Cycloadditions:  The Four-Component [5+1+2+1] Cycloaddition of Vinylcyclopropanes, Alkynes, and CO
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    Stanford University, Department of Chemistry, Stanford, California 94305-5080
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2005, 127, 9, 2836–2837
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    https://doi.org/10.1021/ja042728b
    Published February 11, 2005
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    Abstract

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    Prompted by the view that intermediates of transition metal-catalyzed reactions could be intercepted by one or more additional components, studies in our laboratory have led to the design and development of new three-component [5+2+1], [4+2+1], and [2+2+1] cycloadditions. These continuing studies have now led to the identification of a fundamentally new four-component [5+1+2+1] cycloaddition reaction of vinylcyclopropanes, alkynes and CO, yielding hydroxyindanone products in generally good yields. Terminal alkynes bearing aryl or alkyl groups are tolerated well. Substitution at any position of the VCP leads predictably to substituted hydroxyindanone products. Using a bis-alkynyl substrate, the reaction can be carried out bi-directionally, forming 10 C−C bonds and four new rings from seven components in a single, operationally simple process.

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    Representative procedure and characterization data for products 5, 9, 11, 13, 15. X-ray data for compound 5a in CIF format. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2005, 127, 9, 2836–2837
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