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- Title
Novel and Stereospecific Synthesis of (2 S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol from D-Mannitol.
- Authors
Aktaş, Derya; Fıstıkçı, Meryem; Gündoğdu, Özlem; Seçen, Hasan; Şahin, M. Fethi; Altundaş, Ramazan; Kara, Yunus
- Abstract
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 Ph3P catalyzed reaction of the latter with C2Cl6 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.
- Subjects
STEREOSPECIFICITY; GLYCOL synthesis; PROPANE; CATALYTIC hydrogenation; PALLADIUM catalysts; MANNITOL
- Publication
Helvetica Chimica Acta, 2015, Vol 98, Issue 8, p1127
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201500031