Acyclic stereoselection. 23. Lactaldehyde enolate equivalents
CH Heathcock, MC Pirrung, SD Young…
Index: Heathcock,C.H.; Pirrung,M.C.; Young,S.D. Journal of the American Chemical Society, 1984 , vol. 106, p. 8161
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Citation Number: 48
Abstract
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 ...
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