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Multiple deprotonations of α-hydroxy esters by lithium diisopropylamide lead directly to alkoxy enediolates, which are useful as synthetic intermediates in electrophilic substitution reactions with primary and secondary alkyl halides and sulfonates to form disubstituted α-hydroxy esters, and with carbonyl compounds and ethylene oxide to form substituted glyceric acids and a substituted α-hydroxy-δ-butyrolactone, respectively. © 1977, American Chemical Society. All rights reserved.
author list (cited authors)
Ciochetto, L. J., Bergbreiter, D. E., & Newcomb, M.