Abstract
The stereochemistry of the lithium-liquid ammonia reduction of 2,3-dimethyl-4-hydroxy-2-cyclopentenone is discussed as a function of the acidity of the proton donor. It is shown that the configuration of the resulting 2,3-dimethyl-1,4-dihydroxycyclopentene is determined by competing intra- and intermolecular protonation.
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