Abstract: A number of lactate esters have been synthesized and stereochemistry of the reactions of their enolates with aldehydes examined. Dioxolanones 3 and 4 and oxazolanone 10 show low stereoselectivity (Table I). Methyl esters of various 0-alkylated lactic acids (17-19) show generally higher stereoselectivity (Table 11). Of these reagents, the best is methyl 2-methoxypropanoate (17), which shows exceedingly high selectivity ...
