Novel and Stereospecific Synthesis of (2S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol from D-Mannitol
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.
Atıf için künye
Anıl, D., FISTIKCI, M., GUENDOGDU, O., Seçen, H., SAHIN, M. F., Altundas, R., & Kara, Y. (2015). Novel and Stereospecific Synthesis of (2S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol from D-Mannitol. HELVETICA CHIMICA ACTA, 98(8), 1127–1131. https://doi.org/10.1002/hlca.201500031
BibTeX
@article{anil2015-71390,
author = {Anıl, Derya and FISTIKCI, Meryem and GUENDOGDU, OEzlem and Seçen, Hasan and SAHIN, M. Fethi and Altundas, Ramazan and Kara, Yunus},
title = {Novel and Stereospecific Synthesis of (2S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol from D-Mannitol},
journal = {HELVETICA CHIMICA ACTA},
year = {2015},
volume = {98},
number = {8},
pages = {1127--1131},
issn = {0018-019X},
doi = {10.1002/hlca.201500031},
url = {https://akademik.atauni.edu.tr/yayinlar/71390-novel-and-stereospecific-synthesis-of-2s-3-245-trifluorophenylpropane-12-diol}
}