A chiral Ag-based catalyst for practical, efficient, and highly enantioselective additions of enolsilanes to alpha-ketoesters.
A Ag-based chiral catalyst promotes efficient and highly enantioselective aldol additions of ketone-derived enolsilanes to alpha-ketoesters in the presence of a readily available amino acid-based ligand and commercially available AgF2. alpha-Ketoester substrates may bear alkyl, alkenyl, and aryl substituents; reactions proceed to >98% conversion to afford the desired tertiary alcohols in 61->98% isolated yield and 60-96% ee. In contrast to previously reported approaches, highest enantioselectivities are observed with sterically demanding substrates, and reactions can be carried out in undistilled solvent, in air with as little as 1 mol % catalyst.
Akullian
Laura C
LC
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Snapper
Marc L
ML
Hoveyda
Amir H
AH
D002384:Catalysis; D004952:Esters / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D007659:Ketones; D012821:Silanes; D018030:Silver Compounds; C105022:silver fluoride; D005459:Fluorides