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Gosteli-Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements

  作者 GILLE ANNIKA; REHBEIN JULIA; HIERSEMANN MARTIN  
  选自 期刊  Organic Letters;  卷期  2011年13-8;  页码  2122-2125  
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[摘要]The ambivalent reactivity of 2-alkoxycarbonyl-substituted propargyl vinyl ethers has been explored. Depending on the conditions, the catalyzed and uncatalyzed Gosteli-Claisen rearrangement triggers downstream transformations that cascade from initially formed gamma-allenyl alpha-keto esters to highly substituted furanes and cyclopentenes. In support of a mechanistic hypothesis, the results of a DFT study using the B1B95 and B3LYP functionals are revealed.

 
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