title: Stereoselective Arylation of Amino Aldehydes: Overriding Natural Substrate Control through Chelation.
abstract: The chelation-controlled arylation reaction of chiral, enantiopure acyclic α-amino aldehydes enabled by a B/Zn exchange reaction between arylboronic acids and Et2Zn is reported. The presence of dibenzyl substituents at the nitrogen plays a key role in the stereochemical outcome of the reaction, and chelation is favored over the natural tendency of this type of substrate to undergo Felkin-Anh controlled additions with organomagnesium and organolithium reagents.
authors.affiliation: Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS , Av. Bento Gonçalves 9500, 91501-970, Porto Alegre, RS, Brazil.
authors.forename: Bruna S
authors.initials: BS
authors.lastname: Martins
authors.affiliation: Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS , Av. Bento Gonçalves 9500, 91501-970, Porto Alegre, RS, Brazil.
authors.forename: Angélica V
authors.initials: AV
authors.lastname: Moro
authors.affiliation: Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS , Av. Bento Gonçalves 9500, 91501-970, Porto Alegre, RS, Brazil.
authors.forename: Diogo S
authors.identifier: 0000-0002-9135-4298
authors.initials: DS
authors.lastname: Lüdtke