title: β2, 2-Amino Acid N-Carboxyanhydrides Relying on Sequential Enantioselective C(4)-Functionalization of Pyrrolidin-2,3-diones and Regioselective Baeyer-Villiger Oxidation.
abstract: A catalytic enantioselective entry to β2, 2-amino acids enabling their direct coupling with nucleophiles is described. The approach is based upon an effective bifunctional Brønsted base catalyzed construction of a quaternary carbon stereocenter at C4position of pyrrolidin-2,3-diones. Subsequent regioselective Baeyer-Villiger oxidation of the resultant adducts gives β2, 2-amino acid N-carboxyanhydrides as the reactive species, which can further react with nucleophiles. Following this strategy both, β2, 2-amino acid derivatives with different functionalities at the newly created stereocenter, and spirocyclic structures can be efficiently prepared.
authors.affiliation: Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizábal, 3, 20018, Donostia-San Sebastián, Spain.
authors.forename: Eider
authors.initials: E
authors.lastname: Badiola
authors.affiliation: Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizábal, 3, 20018, Donostia-San Sebastián, Spain.
authors.forename: Iurre
authors.initials: I
authors.lastname: Olaizola
authors.affiliation: Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizábal, 3, 20018, Donostia-San Sebastián, Spain.
authors.forename: Ana
authors.initials: A
authors.lastname: Vázquez
authors.affiliation: Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizábal, 3, 20018, Donostia-San Sebastián, Spain.
authors.forename: Silvia
authors.initials: S
authors.lastname: Vera
authors.affiliation: Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizábal, 3, 20018, Donostia-San Sebastián, Spain.
authors.forename: Antonia
authors.initials: A
authors.lastname: Mielgo
authors.affiliation: Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizábal, 3, 20018, Donostia-San Sebastián, Spain.
authors.forename: Claudio
authors.identifier: http://orcid.org/0000-0001-9809-2799
authors.initials: C
authors.lastname: Palomo
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000812:Anhydrides; D011759:Pyrrolidines; C032519:pyrrolidine
keywords: Brønsted bases; organocatalysis; quaternary centers; synthetic methods; β-amino acids