A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method |
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| Authors: | Derya Anil Ramazan Altundas |
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| Affiliation: | 1. Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, Turkey;2. Department of Chemistry, Faculty of Sciences, Gebze Technical University, Gebze, Turkey |
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| Abstract: | Synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by the Sharpless asymmetric epoxidation reaction has been achieved. 2,4,5-Trifluorobenzaldehyde with methyl 2-(triphenyl-λ5-phosphanylidene)acetate gave methyl (E)-3-(2,4,5-trifluorophenyl)acrylate in 83% yield. The reduction of ester group with DibalH followed by Sharpless asymmetric epoxidation gave ((2R,3R)-3-(2,4,5-trifluorophenyl)oxiran-2-yl)methanol. Pd/C-catalyzed hydrogenation of epoxy alcohol furnished (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >90% ee and 71% yield. |
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| Keywords: | β-hydroxy acid β-amino acid propane-1,2-diol Sharpless asymmetric epoxidation sitagliptin |
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