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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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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cited_by cdi_FETCH-LOGICAL-c3551-fdf489be8b20485f7c37488850a9e87fbf38fe9d349a8535bb97dfb40efee0e63
cites cdi_FETCH-LOGICAL-c3551-fdf489be8b20485f7c37488850a9e87fbf38fe9d349a8535bb97dfb40efee0e63
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container_title Helvetica chimica acta
container_volume 98
creator Aktaş, Derya
Fıstıkçı, Meryem
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Seçen, Hasan
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Kara, Yunus
description 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.
doi_str_mv 10.1002/hlca.201500031
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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 &gt;99% ee and 65% yield.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.201500031</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>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</subject><ispartof>Helvetica chimica acta, 2015-08, Vol.98 (8), p.1127-1131</ispartof><rights>Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich</rights><rights>Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zurich</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3551-fdf489be8b20485f7c37488850a9e87fbf38fe9d349a8535bb97dfb40efee0e63</citedby><cites>FETCH-LOGICAL-c3551-fdf489be8b20485f7c37488850a9e87fbf38fe9d349a8535bb97dfb40efee0e63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Aktaş, Derya</creatorcontrib><creatorcontrib>Fıstıkçı, Meryem</creatorcontrib><creatorcontrib>Gündoğdu, Özlem</creatorcontrib><creatorcontrib>Seçen, Hasan</creatorcontrib><creatorcontrib>Şahin, M. 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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
title Novel and Stereospecific Synthesis of (2S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol from D-Mannitol
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