title: Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis.
abstract: The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding beta-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (-)-8-phenylmenthol as a chiral auxiliary.
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: Juan F
authors.initials: JF
authors.lastname: Sanz-Cervera
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.forename: Carlos
authors.initials: C
authors.lastname: Del Pozo
authors.forename: Begoña
authors.initials: B
authors.lastname: Fernandez
authors.forename: Ana
authors.initials: A
authors.lastname: Bartolomé
authors.forename: Amparo
authors.initials: A
authors.lastname: Asensio
authors.forename: Carmen
authors.initials: C
authors.lastname: Ramírez de Arellano
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D005461:Fluorine / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D005461:Fluorine