| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1313911 | Journal of Fluorine Chemistry | 2012 | 10 Pages |
The intramolecular fluoroamination of homoallylic amines activated by a triisopropylsilyl or p-tolyldiisopropylsilyl group was successfully performed in the presence of Selectfluor® in acetonitrile leading to anti or syn 3-fluoropyrrolidines. The stereochemical outcome of these fluorocyclizations is dictated by the geometry of the alkene precursor. In comparison with oxygen nucleophile, the use of N-tosyl or N-Boc nucleophiles benefits from superior control over stereoselectivity but suffers from competitive fluorodesilylation.
Graphical abstractThe fluoroamination of homoallylic amines activated by a triisopropylsilyl or p-tolyldiisopropylsilyl group is a suitable route to access to anti or syn 3-fluoropyrrolidines. The stereochemical outcome of these fluorocyclizations is dictated by the geometry of the alkene precursor.Figure optionsDownload full-size imageDownload as PowerPoint slide
