title: Asymmetric synthesis of new beta,beta-difluorinated cyclic quaternary alpha-amino acid derivatives.
abstract: The synthesis of new beta,beta-difluorinated cyclic quaternary alpha-amino acid derivatives 1 in which a ring-closing metathesis reaction (RCM) constitutes the key step is described. The approach employs imidoyl chlorides 3 as fluorinated building blocks, and the overall process involves the stereoselective creation of a quaternary stereocenter. Complete selectivity was achieved when (R)-phenylglycinol methyl ether was used as chiral auxiliary, allowing for the preparation of new six-membered cyclic fluorinated alpha-amino acids as single enantiomers.
authors.affiliation: Departamento de Química Organica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
authors.forename: María
authors.initials: M
authors.lastname: Sanchez-Roselló
authors.forename: Vanessa
authors.initials: V
authors.lastname: Rodrigo
authors.forename: Carlos
authors.initials: C
authors.lastname: del Pozo
authors.forename: Juan F
authors.initials: JF
authors.lastname: Sanz-Cervera
authors.forename: Antonio
authors.initials: A
authors.lastname: Simón
authors.forename: Carmen
authors.initials: C
authors.lastname: Ramírez de Arellano
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D005461:Fluorine / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D005461:Fluorine