An enantioselective synthesis of (S)-4-fluorohistidine

We report a new synthesis of enantiomerically pure (S)-4-fluorohisitidine based on diastereoselective alkylation of MOM-protected 4-fluoro-5-bromomethyl imidazole using the Schöllkopf bis-lactim amino acid synthesis. Improvements in procedures for preparation of key intermediates are also described. (S)-4-Fluorohisitidine prepared by this new method was identical in all respects to material prepared by previous procedures.

Graphical abstract(S)-4-Fluorohistidine was synthesized by diastereoselective alkylation of a MOM-protected 4-fluoro-5-bromomethyl imidazole.Figure optionsDownload full-size imageDownload as PowerPoint slide