The lithium enolate (2), readily obtained from the D-mannose derivative (1) at low temperature, reacts with electrophilic reagents in a tetrahydrofuran–hexamethylphosphoric triamide mixture, providing a short rout to 2-C-alkyl sugars; the subsequent enolization–alkylation creates a chiral quaternary carbon centre.
Y. Chapleur, J. Chem. Soc., Chem. Commun., 1983, 141 DOI: 10.1039/C39830000141
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