title: Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: intramolecular pi-stacking interactions as a source of stereocontrol.
abstract: [reaction: see text]. Hydride reduction of C=N bonds stereocontrolled by intramolecular pi-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta-amino alcohols and alpha-amino acid derivatives, respectively.
authors.affiliation: Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, E-46100 Burjassot, Valencia, Spain. santos.fustero@uv.es
authors.forename: S
authors.initials: S
authors.lastname: Fustero
authors.forename: A
authors.initials: A
authors.lastname: Navarro
authors.forename: B
authors.initials: B
authors.lastname: Pina
authors.forename: J G
authors.initials: JG
authors.lastname: Soler
authors.forename: A
authors.initials: A
authors.lastname: Bartolomé
authors.forename: A
authors.initials: A
authors.lastname: Asensio
authors.forename: A
authors.initials: A
authors.lastname: Simón
authors.forename: P
authors.initials: P
authors.lastname: Bravo
authors.forename: G
authors.initials: G
authors.lastname: Fronza
authors.forename: A
authors.initials: A
authors.lastname: Volonterio
authors.forename: M
authors.initials: M
authors.lastname: Zanda
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D005461:Fluorine