A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method
Özet
Synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by the Sharpless asymmetric epoxidation reaction has been achieved. 2,4,5-Trifluorobenzaldehyde with methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate gave methyl (E)-3-(2,4,5-trifluorophenyl)acrylate in 83% yield. The reduction of ester group with DibalH followed by Sharpless asymmetric epoxidation gave ((2R,3R)-3-(2,4,5-trifluorophenyl)oxiran-2-yl)methanol. Pd/C-catalyzed hydrogenation of epoxy alcohol furnished (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >90% ee and 71% yield.
Atıf için künye
Anıl, D., ALTUNDAŞ, R., & Kara, Y. (2019). A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method. SYNTHETIC COMMUNICATIONS, 49(6), 852–858. https://doi.org/10.1080/00397911.2019.1576050
BibTeX
@article{anil2019-72436,
author = {Anıl, Derya and ALTUNDAŞ, RAMAZAN and Kara, Yunus},
title = {A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method},
journal = {SYNTHETIC COMMUNICATIONS},
year = {2019},
volume = {49},
number = {6},
pages = {852--858},
issn = {0039-7911},
doi = {10.1080/00397911.2019.1576050},
url = {https://akademik.atauni.edu.tr/yayinlar/72436-a-novel-synthesis-of-2s-3-245-trifluorophenylpropane-12-diol-by-sharpless}
}