Diastereoselective Addition of Organometallics to α-Keto Esters Bearing chiro-Inositol Derivatives as Chiral Auxiliaries

Abstract

Abstract The nucleophilic addition of organometallics to α-keto esters derived from (1l)-1,2:5,6-di-O-cyclohexylidene-3-t-butyldimethylsilyl-chiro-inositol afforded the corresponding α-hydroxy esters of high diastereomeric excess (up to 98% de). Grignard reagents attacked from re-face, while organolithium reagents preferred si-face attack.