HBF4-catalyzed Mannich-type reaction of silyl enolates with aldimines took place smoothly in aqueous organic solvent to afford β-aminocarbonyl compounds in high yields. The HBF4-catalyzed Mannich-type reaction also proceeded smoothly in water without organic solvent in the presence of a surfactant. A three-component synthesis starting from aldehyde, amine, and silyl enolate was successfully realized by means of a Brønsted acid in aqueous media.
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Akiyama et al. (2002) studied this question.