title: Synthesis of functionalized pyrrole and indole derivatives through carbometallation of lithiated double bonds.
abstract: Bis(2-lithioallyl)amines derived from bis(2-bromoallyl)amines undergo intramolecular carbometallation of a lithiated double bond, giving dilithiated dihydropyrroles. The cyclizations are promoted by N,N,N',N'-tetramethylethylenediamine (TMEDA). Reaction of these intermediates with electrophiles allows the preparation of some new fused and nonfused five-membered functionalized heterocycles. Although 2-lithioallylamines do not suffer intermolecular carbometallation, dimerization products are obtained with their copper or zirconium derivatives. Finally, the application of this new reaction to 2-lithio-N-(2-lithioallyl)anilines leads to 3-lithiomethylindole derivatives, which are transformed to functionalized indole derivatives by reaction with electrophiles.
authors.affiliation: Instituto Universitario de Química Organometálica Enrique Moles, Universidad de Oviedo, Spain.
authors.forename: F J
authors.initials: FJ
authors.lastname: Fañanás
authors.forename: A
authors.initials: A
authors.lastname: Granados
authors.forename: R
authors.initials: R
authors.lastname: Sanz
authors.forename: J M
authors.initials: JM
authors.lastname: Ignacio
authors.forename: J
authors.initials: J
authors.lastname: Barluenga