Gold-Catalyzed Hydrofluorination of Electron-Deficient
Alkynes: Stereoselective Synthesis of β‑Fluoro Michael
Acceptors
Thomas
J. O’Connor
F. Dean Toste
10.1021/acscatal.8b01341.s001
https://acs.figshare.com/articles/journal_contribution/Gold-Catalyzed_Hydrofluorination_of_Electron-Deficient_Alkynes_Stereoselective_Synthesis_of_Fluoro_Michael_Acceptors/6432176
The
gold(I)-catalyzed, stereoselective hydrofluorination of electron-deficient
alkynes with triethylamine trihydrogen fluoride (Et<sub>3</sub>N·3HF)
is described. Fluorinated α,β-unsaturated aldehydes, amides,
esters, ketones, and nitriles were isolated in moderate to good yields
as single diastereomers. In all but four cases, the (<i>Z</i>)-vinyl fluorides were initially formed in ≥97% diastereoselectivity.
This work constitutes the first catalytic example of the diastereoselective
preparation of a variety of β-alkyl, β-fluoro Michael
acceptors from alkynes. Additionally, the described work expands access
to β-aryl, β-fluoro Michael acceptors to the synthesis
of β-fluoro-α,β-unsaturated amides and nitriles.
The monofluoroalkenes formed through this strategy were readily transformed
into other fluorine-containing compounds, and the developed method
was applied to the synthesis of a fluorinated analogue of Exoderil,
a topical antimycotic.
2018-06-04 20:13:39
β- aryl
Stereoselective Synthesis
synthesis
triethylamine trihydrogen fluoride
Gold-Catalyzed Hydrofluorination
fluorine-containing compounds
β- fluoro Michael acceptors
electron-deficient alkynes
nitrile
β- alkyl
amide
Electron-Deficient Alkynes
diastereoselective preparation