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Facile 1,3-diaza-Claisen Rearrangements of Tertiary Allylic Amines Bearing an Electron-Deficient Alkene.

  作者 Aranha, Rachel M.;Bowser, Amy M.;Madalengoitia, Jose S.;  
  选自 期刊  Organic Letters;  卷期  2009年11-3;  页码  575-578  
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[摘要]Tertiary allylic amines with an electron-deficient alkene react with isocyanates and isothiocyanates to give highly substituted ureas and thioureas arising from formal 1,3-diaza-Claisen rearrangements. Isocyanates and isothiocyanates with strong electron-withdrawing groups are more reactive. Similarly, the data suggest that a stronger electron-withdrawing substituent on the alkene favors a faster reaction, but this may be offset by sterics in the cyclic transition state.

 
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