title: On the activation of valerolactam with triflic anhydride: the synthesis of omega-trifluorosulfonamido dipeptides using a transpeptidation reaction under mild conditions.
abstract: The activation of valerolactam with triflic anhydride is studied in detail, initially producing an O-triflated lactam, which rearranges, following the addition of base at higher temperatures, to an N-triflated derivative. This reacts with a series of nucleophiles to produce esters and amides, which are formally dipeptides of omega-amino acids.
authors.affiliation: Supramolecular and Biomolecular Chemistry Laboratory, Chemistry, School of Biomedical and Life Sciences, The University of Surrey, Guildford, UKGU2 7XH. n.kuhnert@surrey.ac.uk
authors.forename: Nikolai
authors.initials: N
authors.lastname: Kuhnert
authors.forename: Ian
authors.initials: I
authors.lastname: Clemens
authors.forename: Rodney
authors.initials: R
authors.lastname: Walsh
mesh_terms: D000812:Anhydrides / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013449:Sulfonamides / Q000737:chemistry
chemical_list: D000812:Anhydrides; D004151:Dipeptides; D007769:Lactams; D013449:Sulfonamides; C511520:valerolactam