title: Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions.
abstract: A three component reductive coupling reaction of a (hetero)aromatic amine, a (hetero)aromatic aldehyde and an electron deficient olefin catalysed by eosin Y under green LED light irradiation, for the direct generation of γ-amino acid derivatives, is described. This new umpolung synthesis of amines, which exploits the high nucleophilicity of a putative α-amino radical intermediate, generated via single electron reduction of the in situ generated imine from the Hantzsch ester terminal reductant, is efficient, operationally simple, broad in scope and offers a complementary strategy to existing synthetic approaches.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK. Darren.dixon@chem.ox.ac.uk.
authors.forename: Angel L
authors.initials: AL
authors.lastname: Fuentes de Arriba
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK. Darren.dixon@chem.ox.ac.uk.
authors.forename: Felix
authors.initials: F
authors.lastname: Urbitsch
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK. Darren.dixon@chem.ox.ac.uk.
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon