Synthesis of L-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam.
[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.
Konas
D W
DW
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA.
Coward
J K
JK
D004563:Electrochemistry; D005461:Fluorine / Q000737:chemistry; D005493:Folic Acid Antagonists / Q000138:chemical synthesis*; D005971:Glutamates / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry*; D013237:Stereoisomerism
D005493:Folic Acid Antagonists; D005971:Glutamates; D007769:Lactams; C097769:4,4-difluoroglutamic acid; D005461:Fluorine