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Allene Relay: Palladium-Catalyzed Bicyclization of Allene-Propargylic Carbonates with Geminal Bis(nucleophile)s

Authors

  • Juntao Ye,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Prof. Dr. Shengming Ma

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    2. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Financial support from the National Natural Science Foundation of China (21232006) and the National Basic Research Program of China (2009CB825300) is greatly appreciated. We thank Minyan Wang in our group for reproducing the results presented in entry 4, Table 2 and entries 2 and 10, Table 3.

Abstract

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In nur einer Stufe ergibt die Titelreaktion Bicyclo[4.3.0]-Gerüste in Ausbeuten bis 85 % über drei aufeinander folgende C-C-Bindungsknüpfungen (siehe Schema; DMF=N,N-Dimethylformamid, DMSO=Dimethylsulfoxid, Ts=4-Toluolsulfonyl). Dabei gelang die effiziente Übertragung von einer Chiralitätsachse auf ein Chiralitätszentrum über π-Allylpalladium-Zwischenstufen. Der Mechanismus dieses Prozesses wird diskutiert.

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