As a result of intramolecular co-ordination of the lithium ion, carbohydrate ester enolates show peculiar properties: decomposition above –70 °C to form alcoholate and ketene, stereoselective alkylation at very low temperature, and, for those containing strongly complexing ligands, inertness towards carbon electrophiles.
H. Kunz and J. Mohr, J. Chem. Soc., Chem. Commun., 1988, 1315 DOI: 10.1039/C39880001315
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