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Fe-Catalyzed Allylic C–C-Bond Activation: Vinylcyclopropanes As Versatile a1,a3,d5-Synthons in Traceless Allylic Substitutions and [3 + 2]-Cycloadditions

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    Fe-Catalyzed Allylic C–C-Bond Activation: Vinylcyclopropanes As Versatile a1,a3,d5-Synthons in Traceless Allylic Substitutions and [3 + 2]-Cycloadditions
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    Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, DE-70569 Stuttgart, Germany
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    Cite this: J. Am. Chem. Soc. 2012, 134, 11, 5048–5051
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    https://doi.org/10.1021/ja300294a
    Published March 7, 2012
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    Abstract

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    The low-valent iron complex Bu4N[Fe(CO)3(NO)] (TBAFe) catalyzes the allylic C–C-bond activation of electron-poor vinyl cyclopropanes to generate synthetically useful a1,a3,d5-synthons which are prone to undergo multiple consecutive reactions. The versatility of this approach is demonstrated by a traceless allylic substitution and a formal [3 + 2] cycloaddition to give either functionalized acyclic products or densely substituted cyclopentanes and pyrrolidines in high yields and regioselectivities.

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    Detailed experimental procedures and characterization of all reported compounds. 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. 2012, 134, 11, 5048–5051
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