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Formal Alkylation of Allenes through Highly Selective Radical Cyclizations of Allene-enes

Authors

  • Rong Zeng,

    1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P.R. China)
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  • Prof. Chunling Fu,

    Corresponding author
    1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P.R. China)
    • Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P.R. China)
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  • Prof. Shengming Ma

    Corresponding author
    1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P.R. China)
    • Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P.R. China)
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  • Financial support is acknowledged from the National Basic Research Program of China (No. 2011CB808700) and the National Natural Science Foundation of China (No. 21072167). S.M. is a Qiu Shi Adjunct Prof. at Zhejiang University. We thank Weiming Yuan in this group for reproducing the results presented in entries 9 and 11 in Table 1 and compound 13 a in Scheme 3.

Abstract

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Radikalischer Ringschluss: In der ersten radikalischen Cyclisierung von Allen-enen wurden Perfluoralkylradikale eingesetzt, um die chemoselektive intermolekulare radikalische Addition des Alkens und die anschließende exo-radikalische Addition an das Allen zu realisieren (siehe Schema). Eine TBAF-vermittelte Dehydroiodierung der Cyclisierungsprodukte liefert Cyclopentane unter erneuter Bildung einer Allengruppe (TBAF=Tetra-n-butylammoniumfluorid).

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