Fluorination of Hydroxyesters with N,N-Diethyl-1,1,2,3,3,3-Hexafluoro Propaneamine |
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Authors: | S. Watanabe T. Fujita M. Sakamoto T. Arai T. Kttazume |
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Affiliation: | 1. Department of Applied Chemistry, Faculty of Engineering, Chiba University, Yayoicho, 260, Chiba, Japan 2. Department of Bioengineering, Tokyo Institute of Technology, Meguro, 152, Tokyo, Japan
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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. To whom correspondence should be addressed. |
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