Asymmetric Addition of Organometallics to Chiral Ketooxazolines. Preparation of Enantiomerically Enriched α-Hydroxy Acids

Article abstract of DOI:10.1021/jo01302a008

Addition of Grignard and organolithium reagents to chiral α-ketooxazolines results in α-substituted α-hydroxyoxazoline derivatives which on hydrolytic removal of the chiral auxiliary groups give rise to α-substituted α-hydroxy acids in 30-87 percent enantiomeric excess (ee).Studies on the various parameters (solvents, temperature, substituents) were undertaken to reach optimum asymmetric induction.