title: Synthesis of quaternary stereogenic centres via stereoselective intermolecular Friedel-Crafts reactions.
abstract: Highly stereoselective Friedel-Crafts reactions have been performed using a chiral anthracene template to control the selectivity of the reaction. In the case of additions to fully substituted N-acyliminium ions, competitive elimination and condensation reactions were observed. Retro-Diels-Alder reaction of one of the reaction products led to a precursor that could be used for the construction of pyroglutamic acids bearing quaternary stereogenic centres.
authors.affiliation: Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, S3 7HF, UK.
authors.forename: Jennifer C
authors.initials: JC
authors.lastname: Ball
authors.forename: Robert
authors.initials: R
authors.lastname: Gleave
authors.forename: Simon
authors.initials: S
authors.lastname: Jones
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D011761:Pyrrolidonecarboxylic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011761:Pyrrolidonecarboxylic Acid