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Novel and Stereospecific Synthesis of (2 S )‐3‐(2,4,5‐Trifluorophenyl)propane‐1,2‐diol from D ‐Mannitol
Author(s) -
Aktaş Derya,
Fıstıkçı Meryem,
Gündoğdu Özlem,
Seçen Hasan,
Şahin M. Fethi,
Altundaş Ramazan,
Kara Yunus
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500031
Subject(s) - chemistry , stereospecificity , diastereomer , yield (engineering) , diol , propane , d mannitol , bromide , methanol , medicinal chemistry , stereochemistry , organic chemistry , catalysis , mannitol , materials science , metallurgy
A stereospecific synthesis of (2 S ) ‐ 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 [(4 R )‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl](2,4,5‐trifluorophenyl)methanol in 65% yield as a mixture of diastereoisomers (1 : 1). The Ph 3 P catalyzed reaction of the latter with C 2 Cl 6 followed by reduction with Pd/C‐catalyzed hydrogenation gave (2 S )‐3‐(2,4,5‐trifluorophenyl)propane‐1,2‐diol with >99% ee and 65% yield.