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32.5.2.2.6 Method 6: Protonation and Deuteration of Enolates

DOI: 10.1055/sos-SD-032-00588

Trauner, D.Science of Synthesis, (200832573.

One of the simplest reactions enolates can undergo is protonation to afford carbonyl compounds that are different from their parent compounds (Scheme 26).[‌66‌‌68‌] The deuteration of enolates is a common way to determine the occurrence and regioselectivity of enolate formation. Caution must be taken with quantifying the degree of deprotonation through a deuteration experiment, since the deuterium source could exchange with a protonated amine base present before the enolate becomes deuterated.

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