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Iron(III)-Catalyzed Consecutive Aza-Cope-Mannich Cyclization: Synthesis of trans-3,5-Dialkyl Pyrrolidines and 3,5-Dialkyl-2,5-dihydro-1H-pyrroles

  作者 CARBALLO RUBEN M; PURINO MARTIN; RAMIREZ MIGUEL A; MARTIN VICTOR S; PADRON JUAN I  
  选自 期刊  Organic Letters;  卷期  2010年12-22;  页码  5334-5337  
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[摘要]An efficient alkene aza-Cope-Mannich cyclization between 2-hydroxy homoallyl tosylamine and aldehydes in the presence of iron(III) salts to obtain 3-alkyl-1-tosyl pyrrolidines in good yields is described. The process is based on the consecutive generation of a gamma-unsaturated iminium ion, 2-azonia-[3,3]-sigmatropic rearrangement, and further intramolecular Mannich reaction. Iron(III) salts are also shown to be excellent catalysts for the new aza-Cope-Mannich cyclization using 2-hydroxy homopropargyl tosylamine.

 
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