Novel and stereospecific synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol from D-mannitol

Aktaş, Derya; Fistikçi, MERYEM; Gündoʇdu, Özlem; SEÇEN, Hasan; Şahin, M.; Altundaş, Ramazan; KARA, Yunus

doi:10.1002/hlca.201500031

Novel and stereospecific synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol from D-mannitol

Aktaş D., Fistikçi M., Gündoʇdu Ö., SEÇEN H., Şahin M. F., Altundaş R., ...Daha Fazla

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
Hakkari Üniversitesi Adresli: Hayır

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.