Abstract
The intramolecular crossed aldehyde–ketone benzoin condensation in the chalcone of o-phthalaldehyde (OPA) catalyzed by N-heterocyclic carbene (NHCs) generated in situ from readily available imidazolium and thiazolium salts is described. In this reaction, bicyclic α-hydroxyl ketones (naphthalenone type tertiary alcohol) were selectively produced in good yields (75–94%) in shorter reaction times (20 min) through nucleophilic addition of acyl anion generated by umpolung in OPA–chalcone (regio controlled).
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