Selective 1,4-Chiral Induction in the Reaction of Enolates Generated from t-Butyl δ-Hydroxy Carboxylates

Article abstract of DOI:10.1246/bcsj.60.1457

Lithium enolates generated from t-butyl esters of δ-hydroxy carboxylic acids with lithium dialkylamides in THF-HMPA were alkylated stereoselectively to give the corresponding syn-α-alkylated δ-hydroxy esters.The generation of the enolates was accelerated by the addition of lithium trifluoromethanesulfonate, and the successive aldol and hydroxylation reactions of the enolates also proceeded in a stereoselective manner.