A pass of electricity (4.0 F mol–1, constant 1.5 A current) through a cell containing β-silyl; cycloalkanone 1,2, or 10 in anhydrous methanol with NaOMe at –10 °C in the anodic chamber gives the corresponding aldols with hydroxymethyl groups exclusively at the α′-position; the silicon β-destabilizing effect on the intermediate enolate ion results in high regioselectivity.
L. C. Lin, Y. C. Li, C. C. Lin and J. R. Hwu, Chem. Commun., 1996, 509 DOI: 10.1039/CC9960000509
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