Enolate alkylation forms a carbon–carbon bond by attack of an enolate carbon on an alkyl electrophile, commonly through an SN2 reaction. Solvent, counterion, aggregation and electrophile identity affect competition with oxygen alkylation.
Conjugate reduction followed by carbon-electrophile trapping of the resulting enolate. The original enone alpha position determines the alkylation site before any later equilibration.
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