Abstract
The reactions of N,N-diethyl-1,1,2,3,3,3-hexafluoro propaneamine (PPDA) with Β-hydroxyl esters gave their corresponding fluorides. For example, methyl (S)-(+)-3-fluorobutyrate was obtained from the reaction of methyl (R)-(-)-3-hydroxybutyrate with PPDA. The reaction ofa-hydroxy esters with PPDA gave a mixture of their corresponding fluorides and 2,3,3,3-tetrafluoropropionate esters. However, γ- and δ-hydroxyesters did not give their fluorinated compounds. Hydrolysis of those racemic monofluoroesters with Lipase MY gave optical active monofluorocarboxylic acids and esters.
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Watanabe, S., Fujita, T., Sakamoto, M. et al. Fluorination of Hydroxyesters with N,N-Diethyl-1,1,2,3,3,3-Hexafluoro Propaneamine. J Am Oil Chem Soc 66, 1312–1315 (1989). https://doi.org/10.1007/BF03022752
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DOI: https://doi.org/10.1007/BF03022752