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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

Tetrahedron , 2011, 67 (17), 3091-3097

DOI: 10.1016/j.tet.2011.02.082

Mykhailiuk P. K.; Shishkina S. V.; Shishkin O. V.; Zaporozhets O. A.; Komarov I. V.

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.

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

Mykhailiuk P. K.; Shishkina S. V.; Shishkin O. V.; Zaporozhets O. A.; Komarov I. V.
Tetrahedron 2011, 67 (17), 3091-3097
DOI: 10.1016/j.tet.2011.02.082

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