Novel and Stereospecific Synthesis of (2S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol from D-Mannitol
HELVETICA CHIMICA ACTA, cilt.98, sa.8, ss.1127-1131, 2015 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 98 Sayı: 8
- Basım Tarihi: 2015
- Doi Numarası: 10.1002/hlca.201500031
- Dergi Adı: HELVETICA CHIMICA ACTA
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1127-1131
- Atatürk Üniversitesi Adresli: Evet
Özet
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.