Electrochemical silicon-directed aldol condensation by a β-destabilizing effect
Abstract
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.