TY - JOUR T1 - Stereoselective aldol additions of achiral ethyl ketone-derived trichlorosilyl enolates. AU - Denmark,Scott E, AU - Pham,Son M, PY - 2003/6/21/pubmed PY - 2003/6/21/medline PY - 2003/6/21/entrez SP - 5045 EP - 55 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 13 N2 - 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. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12816457/Stereoselective_aldol_additions_of_achiral_ethyl_ketone_derived_trichlorosilyl_enolates_ DB - PRIME DP - Unbound Medicine ER -