A novel synthesis of (2S)-3-(2, 4, 5-trifluorophenyl)propane-1, 2-diol by sharpless asymmetric epoxidation method. Issue 6 (19th March 2019)

• Record Type: Journal Article
• Authors: Anil, Derya; Altundas, Ramazan; Kara, Yunus
• Is Part Of: Synthetic communications. Volume 49:Issue 6(2019)
• Page Start: 852
• Page End: 858
• Publication Date: 2019-03-19
• Subjects: β-hydroxy acid -- β-amino acid -- propane-1, 2-diol -- Sharpless asymmetric epoxidation -- sitagliptin; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2019.1576050
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Synthesis of (2 S )-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-λ 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 ((2 R, 3 R )-3-(2, 4, 5-trifluorophenyl)oxiran-2-yl)methanol. Pd/C-catalyzed hydrogenation of epoxy alcohol furnished (2 S )-3-(2, 4, 5-trifluorophenyl)propane-1, 2-diol with >90% ee and 71% yield. Graphical Abstract: