1255312-77-6Relevant articles and documents
Iron(III)-catalyzed consecutive aza-cope-mannich cyclization: Synthesis of trans -3,5-dialkyl pyrrolidines and 3,5-dialkyl-2,5-dihydro-1 H-pyrroles
Carballo, Ruben M.,Purino, Martin,Ramirez, Miguel A.,Martin, Victor S.,Padron, Juan I.
supporting information; experimental part, p. 5334 - 5337 (2011/01/05)
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 γ-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.