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Electro-Organocatalysis: Enantioselective alpha-Alkylation of Aldehydes

  作者 HO XUANHUONG; MHO SUNIL; KANG HYUK; JANG HYEYOUNG  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-23;  页码  4436-4441  
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[摘要]The asymmetric organocatalyzed alpha-alkylation of aldehydes via a cationic radical enamine intermediate was performed under environmentally benign electro-oxidation conditions without the use of chemical oxidants To promote the desired a-alkylation reaction of aldehydes, various aldehydes with xanthene or cycloheptatriene groups were exposed to electro-organocatalytic conditions to afford optically active usubstituted aldehydes (alpha-alkylated aldehydes) in good yield A reaction mechanism involving the cationic radical enamine was proposed based on the cyclic voltammetry (CV) results, DFT calculations, and control experiments.

 
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