| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1314099 | Journal of Fluorine Chemistry | 2012 | 6 Pages |
The alkylation reactions of an amide sodium enolate derived from a C-2 disubstituted trifluoromethylated oxazolidine (Fox) chiral auxiliary occurred in good yields with a very high diastereoselectivity (>98% de). Compared to the C-2 monosubstituted trifluoromethyl analogue, this chiral auxiliary is much more stable towards bases at temperature over −35 °C because the dehydrofluorination reaction is avoided. However asymmetric enolates quaternarization was not successfully achieved with this new chiral auxiliary.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Highly diastereoselective (>98% de) alkylation of amide enolates ► Stable chiral auxiliary because the dehydrofluorination reaction is avoided ► The removal of the chiral auxiliary provides an enantiopure hydroxy compound.
