Gold(I)-Catalyzed Cycloisomerization of 1,6-Diynes: Synthesis of 2,3-Disubstituted 3-Pyrroline Derivatives

Authors

  • Di-Han Zhang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Liang-Feng Yao,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Yin Wei,

  • Prof. Min Shi

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • We thank the Shanghai Municipal Committee of Science and Technology (08dj1400100-2), the National Basic Research Program of China (973)-2009CB825300, and the National Natural Science Foundation of China for financial support (21072206, 20472096, 20872162, 20672127, 20821002, and 20732008).

Abstract

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A novel synthetic protocol for the preparation of the title compounds has been developed from a gold-catalyzed cycloisomerization of 1,6-diynes containing propargylic ester and arene–yne units. The corresponding nitrogen-containing five-membered heterocyclic compounds have been obtained in moderate to good yields (see scheme; DCE=1,2-dichloroethane, Tf=triflate). A plausible reaction mechanism has been proposed on the basis of deuterium labeling experiments.

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