1,3-Dipolar Addition of Methyl α-Diazoacetoacetate to Enamines: A New Synthetic Route to 5-Amino-4,5-dihydrofurans  

作　　者：黄丹 鄢明 赵伟杰 沈琪 

机构地区：[1]Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226007, China [2]Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China

出　　处：《Chinese Journal of Chemistry》2004年第12期1407-1412,共6页中国化学（英文版）

基　　金：Project supported by the National Natural Science Foundation of China (No. 20472061); Suzhou University (No. Q4109308) and the Key Laboratory of Organic Synthesis of Jiangsu Province (No. JSK004).

摘　　要：The reaction of methyl α-diazoacetoacetate with enamines catalyzed by dirhodium and copper complexes un-derwent formal 1,3-dipolar addition to give 5-amino-4,5-dihydrofurans in moderate yields. The reaction was sug-gested to proceed via a nucleophilic addition of enamines to metal-carbenes and a subsequent intramolecular cycli-zation of the resulting zwitterionic intermediates.The reaction of methyl α-diazoacetoacetate with enamines catalyzed by dirhodium and copper complexes un-derwent formal 1,3-dipolar addition to give 5-amino-4,5-dihydrofurans in moderate yields. The reaction was sug-gested to proceed via a nucleophilic addition of enamines to metal-carbenes and a subsequent intramolecular cycli-zation of the resulting zwitterionic intermediates.

关 键 词：DIHYDROFURAN enamine 1 3-dipolar addition diazoacetoacetate catalysis 

分 类 号：O621[理学—有机化学]