Exploiting morph-DAST mediated ring-expansion of substituted cyclic β-amino alcohols for the preparation of cyclic fluorinated amino acids. Synthesis of 5-fluoromethylproline and 5-fluoropipecolic acid

The synthesis of proline analogues bearing a fluorine-containing substituent at the fifth position of the pyrrolidine ring, racemic trans- and cis-5-fluoromethyl prolines, was performed. The key step of the synthesis is a transformation of the CH2OH-group into the CH2F-one using morpholinosulfur trifluoride. During the synthesis, an efficient procedure to prepare trans- and cis-5-fluoropipecolic acids was elaborated.