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22.1.3.1.4 Method 4: Alkoxythiocarboxylation of Enolates

DOI: 10.1055/sos-SD-022-00101

Glass, R. S.Science of Synthesis, (20052292.

Ketones in the presence of O-alkyl S-methyl dithiocarbonates and either sodium tert-butoxide in tert-butyl alcohol[‌19‌] or sodium amide in toluene[‌20‌] at room temperature produce α-oxo thiocarboxylic O-acid esters 10 after acidification (Scheme 10). These products preferentially exist as the enol tautomers. Similarly, [(dimethoxyphosphoryl)methyl]copper is alkoxythioacylated with O-alkyl chlorothioformates.[‌21‌]

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