Title of article :
Intramolecular Carbolithiation of Aromatic N-Allyl-N-(2-Lithioallyl)Amines:Reinvestigation of the Mechanism and Synthesis of Functionalized Pyrrolidines
Author/Authors :
Sanz, Roberto Universidad de Burgos - Facultad de Ciencias ,Departamento de Química - Área de Química Orgánica, Spain , Castroviejoa, M Pilar Universidad de Burgos - Facultad de Ciencias - Departamento de Química, Área de Química Orgánica, Spain , Miguel, Delia Universidad de Burgos - Facultad de Ciencias - Departamento de Química, Área de Química Orgánica, Spain , Fañanás, Francisco J. Universidadde Oviedo - Instituto Universitario de Química Organometálica “Enrique Moles” - Unidad Asociada al C S I C, Spain
Abstract :
The intramolecular carbolithiation reactions of aromatic N-allyl-N-(2-lithioallyl)amines have been studied in detail. Although we have initially proposed a 6-endo ring closure for these substrates, we have found that the course of these processes starts with a 5-exo cyclization reaction. Interestingly, 3-functionalized-4-methylenepyrrolidines have been synthesized from simple starting materials.
Keywords :
Carbolithiation reactions , organolithiums , 5 , exo cyclizations , pyrrolidines
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
