Novel and Stereospecific Synthesis of (2S)‐3‐(2,4,5‐Trifluorophenyl)propane‐1,2‐diol from D‐Mannitol |
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| Authors: | Derya Aktaş Meryem Fıstıkçı Özlem Gündoğdu Hasan Seçen M. Fethi Şahin Ramazan Altundaş Yunus Kara |
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| Affiliation: | 1. Department of Chemistry Faculty of Sciences, Ataturk University, TR‐25240 Erzurum, (fax: +90‐442‐2314109);2. Department of Pharmaceutial Research and Development, FARGEM Inc., Sancaklar, TR‐81100 Duzce |
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| Abstract: | A stereospecific synthesis of (2S)‐3‐(2,4,5‐trifluorophenyl)propane‐1,2‐diol from D ‐mannitol has been developed. The reaction of 2,3‐O‐isopropylidene‐D ‐glyceraldehyde with 2,4,5‐trifluorophenylmagnesium bromide gave [(4R)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl](2,4,5‐trifluorophenyl)methanol in 65% yield as a mixture of diastereoisomers (1 : 1). The Ph3P catalyzed reaction of the latter with C2Cl6 followed by reduction with Pd/C‐catalyzed hydrogenation gave (2S)‐3‐(2,4,5‐trifluorophenyl)propane‐1,2‐diol with >99% ee and 65% yield. |
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| Keywords: | D‐Glyceraldehyde, 2,3‐O‐isopropylidene‐ β ‐Hydroxy acids Propane‐1,2‐diol, 3‐phenyl‐ Trifluorophenylmagnesium bromide |
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