title: Synthesis of L-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam.
abstract: [formula: see text] An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor 48109, USA.
authors.forename: D W
authors.initials: DW
authors.lastname: Konas
authors.forename: J K
authors.initials: JK
authors.lastname: Coward
mesh_terms: D004563:Electrochemistry; D005461:Fluorine / Q000737:chemistry; D005493:Folic Acid Antagonists / Q000138:chemical synthesis*; D005971:Glutamates / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005493:Folic Acid Antagonists; D005971:Glutamates; D007769:Lactams; C097769:4,4-difluoroglutamic acid; D005461:Fluorine