K. Grozinger, R. Kriwacki, S. Leonard
1993
Citations
0
Influential Citations
20
Citations
Journal
Journal of Organic Chemistry
Abstract
A method is described for the α-enantioretentive methylation of L-histidine (S) to give (S)-(+)-α-(fluoromethyl)histidine (8). The synthesis involves the conversion of N im -trityl-L-histidine methyl ester (1) to both the «trans»-(2S,4S)- and «cis»-(2R,4S)-2-(1,1-dimethylethyl)-1-methyl-1,3-imidazolidin-5-one analogs 4 and 5. The cis isomer was regioselectively alkylated with chlorofluoromethane to give a single diastereomer 6 with retention of the original absolute configuration of the histidine α-position (S)