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 |
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Authors: | Pavel K Mykhailiuk Svetlana V ShishkinaOleg V Shishkin Olga A ZaporozhetsIgor V Komarov |
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Institution: | a Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine b Department of Chemistry, Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, 01033 Kyiv, Ukraine c STC, ‘Institute for Single Crystals’, National Academy of Science of Ukraine, 60 Lenina Ave., Kharkiv 61001, Ukraine |
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Abstract: | 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. |
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Keywords: | Amino acids Fluorine Morph-DAST Proline Pipecolic acid |
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