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Umpolung of Hemiaminals: Titanocene-Catalyzed Dehydroxylative Radical Coupling Reactions with Activated Alkenes

Authors

  • Assoc. Prof. Dr. Xiao Zheng,

    Corresponding author
    1. Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
    2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (P.R. China)
    • Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • Xi-Jie Dai,

    1. Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • Hong-Qiu Yuan,

    1. Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • Chen-Xi Ye,

    1. Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • Jie Ma,

    1. Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • Prof. Pei-Qiang Huang

    1. Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • We are grateful to the National Basic Research Program (973 Program) of China (Grant No. 2010CB833200), the NSF of China (21172183), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT), the Natural Science Foundation of Fujian Province of China (No. 2010J01050), the Fundamental Research Funds for the Central Universities (No. CXB2011015), and NFFTBS (No. J1210014) for financial support. We also thank Prof. Lin-Feng Xie and Dr. Ai-E Wang of XMU for kind and helpful discussions on this paper.

Abstract

original image

Eine radikalische Kupplung, die vermutlich über eine In-situ-Chlorierung einer Hydroxygruppe mit Me3SiCl verläuft, wird für den Aufbau quartärer Kohlenstoffzentren mit Aminogruppen in α-Position verwendet. Die Reaktion wurde in einer sechsstufigen Totalsynthese von (±)-9,10-Diepistemoamid verwendet (siehe Schema, Cp=Cyclopentadienyl, EWG=elektronenziehende Gruppe).

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