- A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method
-
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-λ5-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.
- Anil, Derya,Altundas, Ramazan,Kara, Yunus
-
-
Read Online
- Novel and stereospecific synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol from D-mannitol
-
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.
- Akta?, Derya,Fistik?i, Meryem,Gündo?du, ?zlem,Se?en, Hasan,?ahin, M. Fethi,Altunda?, Ramazan,Kara, Yunus
-
-
Read Online
- Novel and enantioselective syntheses of (R)- and (S)-3-hydroxy-4-(2,4,5- trifluorophenyl)butanoic acid: A synthon for sitagliptin and its derivatives
-
A new synthetic strategy for (R)- and (S)-3-hydroxy-4-(2,4,5- trifluorophenyl)butanoic acid, a building block in the preparation of sitagliptin and its derivatives, was developed. Pd(OAc)2 catalyzed coupling of 2,4,5-trifluoro-1-iodobenzene wit
- Fistikci, Meryem,Gundogdu, Ozlem,Aktas, Derya,Secen, Hasan,Sahin, M. Fethi,Altundas, Ramazan,Kara, Yunus
-
p. 2607 - 2610
(2012/05/20)
-