Rhodium-Catalyzed Carbonylative [3+3+1] Cycloaddition of Biscyclopropanes with a Vinyl Substituent To Form Seven-Membered Rings

Authors

  • Sun Young Kim,

    1. Intellectual Textile System Research Center, Department of Chemistry, College of National Sciences, Seoul National University, Seoul 151-747, Korea, Fax: (+82) 2-889-0310
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  • Sang Ick Lee,

    1. Intellectual Textile System Research Center, Department of Chemistry, College of National Sciences, Seoul National University, Seoul 151-747, Korea, Fax: (+82) 2-889-0310
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  • Soo Young Choi,

    1. Intellectual Textile System Research Center, Department of Chemistry, College of National Sciences, Seoul National University, Seoul 151-747, Korea, Fax: (+82) 2-889-0310
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  • Young Keun Chung Prof.

    1. Intellectual Textile System Research Center, Department of Chemistry, College of National Sciences, Seoul National University, Seoul 151-747, Korea, Fax: (+82) 2-889-0310
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  • This research was supported by a Korea Research Foundation grant funded by the Korean Government (MOEHRD) (KRF-2008-341-C00022 and KRF-2005-070-C00072) and the SRC/ERC program of MOST/KOSEF (R11-2005-065). S.Y.K. and S.Y.C. are grateful for Brain Korea 21 Fellowships and Seoul Science Fellowships.

Abstract

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Choose your catalyst wisely: Depending on the position of the cyclopropyl substituent on the bicyclo[4.1.0]hept-2-ene substrate, a different rhodium complex was used to catalyze the title reaction, which leads to bicyclic dienones in reasonable to excellent yields (see scheme). The products contain a highly substituted seven-membered ring with useful functionality for further manipulation. R1=H, Me; R2=H, Me, Ph; R3=Me, Et; X=NR, O.

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