Allylic protection of thiols and cysteine: II: The N-[2,3,5,6- tetrafluoro-4-(N'-piperidino)-phenyl], N-allyloxycarbonylaminomethyl (Fnam) group

Article abstract of DOI:10.1016/S0040-4020(99)00323-3

S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)-phenyl], N- allyloxycarbonyl]-aminomethyl (Fnam) derivatives of thiols in general and cysteine in particular are readily deprotected by palladium catalysed allylic cleavage in the presence of various nucleophilic species. They are perfectly stable in both the basic conditions (piperidine/DMF) of Fmoc group removal and the acidic conditions (TFA/CH₂Cl₂) of t-Bu and Boc group removal.