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

AKTAS D., FISTIKCI M., GUENDOGDU O., SEÇEN H., SAHIN M. F., Altundas R., ...Daha Fazla

HELVETICA CHIMICA ACTA, cilt.98, sa.8, ss.1127-1131, 2015 (SCI-Expanded) identifier identifier

  • 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.