Abstract
A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 392-393 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 124 |
| Issue number | 3 |
| DOIs | |
| State | Published - Jan 23 2002 |
| Externally published | Yes |
ASJC Scopus subject areas
- Chemistry(all)
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Evans, D. A., Tedrow, J. S., Shaw, J. T., & Downey, C. W. (2002). Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. Journal of the American Chemical Society, 124(3), 392-393. https://doi.org/10.1021/ja0119548