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Brønsted Acid‐Catalyzed Mannich‐Type Reactions in Aqueous Media
Author(s) -
Akiyama Takahiko,
Takaya Jun,
Kagoshima Hirotaka
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200206)344:3/4<338::aid-adsc338>3.0.co;2-o
Subject(s) - chemistry , silylation , aldehyde , brønsted–lowry acid–base theory , catalysis , mannich reaction , aldimine , aqueous solution , organic chemistry , amine gas treating , solvent , aqueous medium , organocatalysis , organic solvent , enantioselective synthesis , chemical engineering , engineering
HBF 4 ‐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 HBF 4 ‐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.