Gold-Catalyzed Cycloisomerization of Yne-Vinylidenecyclopropanes: A Three-Carbon Synthon for [3+2] Cycloadditions

Authors

  • Wei Yuan,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 (P. R. China), Fax: (+86) 21-64166128
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  • Xiangying Tang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 (P. R. China), Fax: (+86) 21-64166128
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  • Yin Wei,

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 (P. R. China), Fax: (+86) 21-64166128
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 (P. R. China), Fax: (+86) 21-64166128

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  • Min Shi

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 (P. R. China), Fax: (+86) 21-64166128
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 (P. R. China), Fax: (+86) 21-64166128

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Abstract

A novel type of yne-vinylidenecyclopropanes (VDCPs) has been synthesized and applied in gold-catalyzed cycloisomerization reactions. It was found that these compounds can undergo an intramolecular cycloisomerization and perform as a three-carbon synthon for [3+2] cycloaddition under gold catalysis to give fused [4.3.0] and [5.3.0] bicyclic derivatives and VDCP rearranged products in moderated to good yields under mild conditions. The substrate scope of these novel transformations has been explored and plausible reaction mechanisms have been presented on the basis of deuterium labeling experiments and DFT calculations.

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