title: Chiral brønsted Acid-catalyzed stereoselective Mannich-type reaction of azlactones with aldimines.
abstract: A highly diastereo- and enantioselective Mannich-type reaction of azlactones with aldimines catalyzed by a chiral phosphoric acid is described. Only 3 mol % catalyst was required to prepare the Mannich adducts in good yields with high stereochemical control (up to >19:1 dr, >99:1 er). Moreover, the final product contains two consecutive stereogenic centers, one of which is quaternary.
authors.affiliation: Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
authors.forename: Eloah P
authors.initials: EP
authors.lastname: Ávila
authors.affiliation: Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
authors.forename: Rodrigo M S
authors.initials: RM
authors.lastname: Justo
authors.affiliation: Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
authors.forename: Vanessa P
authors.initials: VP
authors.lastname: Gonçalves
authors.affiliation: Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
authors.forename: Adriane A
authors.initials: AA
authors.lastname: Pereira
authors.affiliation: Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
authors.forename: Renata
authors.initials: R
authors.lastname: Diniz
authors.affiliation: Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
authors.forename: Giovanni W
authors.initials: GW
authors.lastname: Amarante
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines; D007783:Lactones; D010756:Phosphoric Acids; C030242:phosphoric acid