title: A concise route to beta-Cyclopropyl amino acids utilizing 1,2-dioxines and stabilized phosphonate nucleophiles.
abstract: 1,2-Dioxines react with glycine-derived phosphonate nucleophiles via a multistep cascade reaction to give beta-cyclopropyl amino acid derivatives in good yield with excellent control of the cyclopropane stereocentres. The cyclopropyl ketones were oxidized to the corresponding carboxylic esters using Baeyer-Villiger conditions. Standard deprotection protocols produced a series of known beta-cyclopropyl amino acids that are selective and potent agonists or antagonists of the metabotropic glutamate receptors in excellent yields.
authors.affiliation: Department of Chemistry, The University of Adelaide, South Australia 5005, Australia.
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Avery
authors.forename: Ben W
authors.initials: BW
authors.lastname: Greatrex
authors.forename: Daniel Sejer
authors.initials: DS
authors.lastname: Pedersen
authors.forename: Dennis K
authors.initials: DK
authors.lastname: Taylor
authors.forename: Edward R T
authors.initials: ER
authors.lastname: Tiekink
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry*; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003521:Cyclopropanes; D004146:Dioxanes; D009943:Organophosphorus Compounds