On the activation of valerolactam with triflic anhydride: the synthesis of omega-trifluorosulfonamido dipeptides using a transpeptidation reaction under mild conditions.
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.
Kuhnert
Nikolai
N
Supramolecular and Biomolecular Chemistry Laboratory, Chemistry, School of Biomedical and Life Sciences, The University of Surrey, Guildford, UKGU2 7XH. n.kuhnert@surrey.ac.uk
Clemens
Ian
I
Walsh
Rodney
R
D000812:Anhydrides / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013449:Sulfonamides / Q000737:chemistry
D000812:Anhydrides; D004151:Dipeptides; D007769:Lactams; D013449:Sulfonamides; C511520:valerolactam