Intermolecular reaction of internal alkynes and imines: propargyl tosylates as key partners in a gold-catalyzed [4 + 1] unusual cyclization leading to cyclopent-2-enimines.
Propargyl tosylates react with N-tosylaldimines to afford cyclopent-2-enimines in a gold-catalyzed process that involves a deep reorganization of both substrates. The formal [4 + 1] cyclization is initiated by a 1,2-migration of the tosylate that eventually generates a substituted 1,3-diene. Subsequent interaction with the imine launches a series of reaction steps prior to a Nazarov-like cyclization to yield the final product.
Suárez-Pantiga
Samuel
S
Instituto Universitario de Química Organometálica Enrique Moles-Unidad Asociada al C.S.I.C. and Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Claveria, 8, 33006 Oviedo, Spain.
Rubio
Eduardo
E
Alvarez-Rúa
Carmen
C
González
José M
JM
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
D000480:Alkynes; D007097:Imines; D014105:Tosyl Compounds; D006046:Gold