D. Baba et al., Electroytic partial fluorination of organic compounds. 52. Regio- and diastereoselective anodic fluorination of thiazolidines, J ORG CHEM, 66(21), 2001, pp. 7020-7024
Anodic fluorination of N-benzoyl, N-acethyl-, and N-formylthiazolidine deri
ved from L-cysteine was carried out in dimethoxyethane (DME) and acetonitri
le containing various supporting fluoride salts using an undivided cell. Hi
ghly regioselective fluorination proceeded to provide the corresponding 5-m
onofluorinated thiazolidine derivatives in good yields in DME, and the dias
tereoselectivitiy was moderate to high regardless of the supporting fluorid
e salts. The diastereoselectivitiy of the fluorination was greatly affected
by the bulkyness of the subsitituent on the nitrogen atom, and N-benzoylth
iazolidine gave much higher diastereoselectivity compared with N-formyl der
ivative. The fluorination of the thiazolidines was not achieved by commerci
ally available fluorinating reagents such as N-fluoropyridinium salts.