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Cu(I)- and Cu(II)-Catalyzed Cyclo- and Michael Addition Reactions of Unsaturated beta-Ketoesters

  作者 SCHOTES CHRISTOPH; MEZZETTI ANTONIO  
  选自 期刊  Journal of Organic Chemistry;  卷期  2011年76-14;  页码  5862-5866  
  关联知识点  
 

[摘要]The alpha-alkylidene beta-ketoesters 2-carbethoxycyclopentenone (la) and ethyl 2-benzoylacrylate (1b) react with 1,2-dimethylbutadiene (2.) (Diels Alder), N-benzyl-N-(cyclohexylethynyl)-4-methylbenzenesulfonamide (3) (Ficini reaction), ethynyl(phenyl)sulfane (4) ([2 + 2] cycloaddition), and 1,2,5trimethyl-1H-pyrrole (5) (Michael addition) in the presence of copper(I) (6) or copper(II) triflate (7) (1-2 mol %) in dichloromethane. This convenient protocol converts 1a and 1b to the corresponding cycloaddition (8-10) or Michael addition (11) products in good yields after reaction times of 0.5-3 h without requiring purified solvents or inert gas atmosphere.

 
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