1,3-dipolar addition of methyl α-diazoacetoacetate to enamines: A new synthetic route to 5-amino-4,5-dihydrofurans
Dan Huang
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
Search for more papers by this authorMing Yan
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China
Search for more papers by this authorWei-Jie Zhao
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China
Search for more papers by this authorQi Shen
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China
Search for more papers by this authorDan Huang
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
Search for more papers by this authorMing Yan
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China
Search for more papers by this authorWei-Jie Zhao
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China
Search for more papers by this authorQi Shen
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China
Search for more papers by this authorAbstract
The reaction of methyl a-diazoacetoacetate with enamines catalyzed by dirhodium and copper complexes underwent formal 1,3-dipolar addition to give 5-amino-4,5-dihydrofurans in moderate yields. The reaction was suggested to proceed via a nucleophilic addition of enamines to metal-carbenes and a subsequent intramolecular cyclization of the resulting zwitterionic intermediates.
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