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Progress in Carbonylative [2+2+1] Cycloaddition: Utilization of a Nitrile Group as the π Component

Authors

  • Takashi Iwata,

    1. Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan)
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  • Dr. Fuyuhiko Inagaki,

    1. Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan)
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  • Prof. Dr. Chisato Mukai

    Corresponding author
    1. Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan)
    • Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan)

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  • This work was supported in part by a Grant-in Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Japan), for which we are thankful.

Abstract

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New tricks, old reactions: The treatment of 2-(1,2-propadienyl)phenylacetonitrile derivatives with a catalytic amount of [{RhCl(CO)dppp}2] (dppp=1,3-bis(diphenylphosphanyl)propane) under a CO atmosphere produced benzo[f]oxyindole derivatives (see scheme). This aza-Pauson–Khand-type reaction was applicable to aliphatic substrates, thus resulting in the formation of the azabicyclo[3.3.0]octadienone derivatives.

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