Abstract

Lewis acid catalysis in aqueous media presents a formidable challenge because of catalyst instability and potential Lewis acid-Lewis base interactions with water. The authors report a scandium-catalyzed hydroxymethylation of silyl enolates with formaldehyde and water as the only solvent. A broad range of silenolethers react with high enantioselectivities. The method is applied to the synthesis of an artificial odorant.

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