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24.2.6.1.3 Method 3: O-Heteroacylation of Ester Enolates

DOI: 10.1055/sos-SD-024-00344

Schneider, C.Science of Synthesis, (200624299.

Ester enolates are ambident nucleophiles that typically react with electrophiles at the carbon atom, with restoration of the ester moiety. However, with some electrophiles the reaction takes place at the oxygen atom to form a ketene O,O-acetal. Thus, lithium ester enolates 18 react with carbon disulfide and an alkyl halide to form O-(1-alkoxyvinyl) S-alkyl dithiocarbonates 19 in typically excellent yields (Scheme 10).[‌19‌]

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