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Evaluation of Catalyst Acidity and Substrate Electronic Effects in a Hydrogen Bond-Catalyzed Enantioselective Reaction

  作者 JENSEN KATRINA H; SIGMAN MATTHEW S  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-21;  页码  7194-7201  
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[摘要]A modular catalyst structure was applied to evaluate the effects of catalyst acidity in a hydrogen bond-catalyzed hetero Diets-Alder reaction. Linear free energy relationships between catalyst acidity and both rate and enantioselectivity were observed, where greater catalyst acidity leads to increased activity and enantioselectivity. A relationship between reactant electronic nature and rate was also observed, although there is no such correlation to enantioselectivity, indicating the system is under catalyst control.

 
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