Novel and Stereospecific Synthesis of (2S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol from D-Mannitol

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...

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Bibliographic Details
Published in:Helvetica chimica acta 2015-08, Vol.98 (8), p.1127-1131
Main Authors: Aktaş, Derya, Fıstıkçı, Meryem, Gündoğdu, Özlem, Seçen, Hasan, Şahin, M. Fethi, Altundaş, Ramazan, Kara, Yunus
Format: Article
Language:English
Subjects:
2-diol
3-O-isopropylidene
3-phenyl
D-Glyceraldehyde
D‐Glyceraldehyde, 2,3‐O‐isopropylidene
Propane
Propane-1
Propane‐1,2‐diol, 3‐phenyl
Trifluorophenylmagnesium bromide
β-Hydroxy acids
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Summary: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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201500031