title: Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides.
abstract: A silver-catalyzed 1,3-dipolar cycloaddition of fluorinated azomethine ylides and activated olefins is reported. The reaction offers a straightforward and atom-economical procedure for the preparation of fluorinated pyrrolidines. Broad scope and high levels of diastereoselectivity have been achieved simply by using AgOAc/PPh3 as the catalyst system. The high efficiency of the cycloaddition relies on the presence of a metal-coordinating group on the imine moiety, such as an ester or heteroaryl group. The asymmetric version of the cycloaddition has been developed by using Taniaphos as a chiral ligand.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049, Madrid, Spain.
authors.forename: Alberto
authors.initials: A
authors.lastname: Ponce
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049, Madrid, Spain.
authors.forename: Inés
authors.identifier: http://orcid.org/0000-0002-5556-5995
authors.initials: I
authors.lastname: Alonso
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049, Madrid, Spain. javier.adrio@uam.es.
authors.forename: Javier
authors.identifier: http://orcid.org/0000-0001-6238-6533
authors.initials: J
authors.lastname: Adrio
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049, Madrid, Spain. juancarlos.carretero@uam.es.
authors.forename: Juan C
authors.identifier: http://orcid.org/0000-0003-4822-5447
authors.initials: JC
authors.lastname: Carretero
keywords: asymmetric catalysis; cycloaddition; fluorinated pyrrolidines; silver; ylides