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Stereoselective aldol additions of achiral ethyl ketone-derived trichlorosilyl enolates.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2003 Jun 27; Vol. 68 (13), pp. 5045-55. - Publication Year :
- 2003
-
Abstract
- Methods for the preparation of geometrically defined enoxy(trichlorosilanes) derived from ethyl ketone enolates have been developed. The addition of enoxy(trichlorosilanes) (trichlorosilyl enolates) to aldehydes proceeds with good yields in the presence of catalytic amounts of chiral phosphoramides. The reaction of Z-trichlorosilyl enolates to aryl aldehydes affords aldol products with good to excellent diastereo- and enantioselectivities. Phosphoramide-catalyzed aldol additions lacked substrate generality providing modest selectivities with unsaturated and aliphatic aldehydes. In all cases, the phosphoramide-catalyzed aldol addition of E-trichlorosilyl enolates to aldehydes provided good yields with moderate to good stereoselectivities.
Details
- Language :
- English
- ISSN :
- 0022-3263
- Volume :
- 68
- Issue :
- 13
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 12816457
- Full Text :
- https://doi.org/10.1021/jo034092x