2005
DOI: 10.1055/s-2004-836062
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HCl-Catalyzed Stereoselective Mannich Reaction in H2O-SDS System

Abstract: HCl-catalyzed Mannich reaction of cyclic ketone, aromatic aldehyde, and aromatic amine proceeded smoothly in water in the presence of SDS to afford the corresponding b-amino ketone with high anti selectivity.

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Cited by 83 publications
(29 citation statements)
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“…4 Numerous versions of the Mannich reaction have been developed 5 in the past. Conventional catalysts for the classical Mannich reaction 6 of aldehydes, ketone and amines involve mainly Lewis acids, 7-9 Bronsted acids [10][11][12] and Lewis base catalysis. 13 However, sodium tetrakis (3,5-trifluoromethylphenyl)borate, 14 scandium tris (dodecanesulfonate), 15 organometalic, 16 ionic liquids 17,18 and recently NbCl 5 19 have also been found to catalyze this reaction.…”
Section: Introductionmentioning
confidence: 99%
“…4 Numerous versions of the Mannich reaction have been developed 5 in the past. Conventional catalysts for the classical Mannich reaction 6 of aldehydes, ketone and amines involve mainly Lewis acids, 7-9 Bronsted acids [10][11][12] and Lewis base catalysis. 13 However, sodium tetrakis (3,5-trifluoromethylphenyl)borate, 14 scandium tris (dodecanesulfonate), 15 organometalic, 16 ionic liquids 17,18 and recently NbCl 5 19 have also been found to catalyze this reaction.…”
Section: Introductionmentioning
confidence: 99%
“…This has led organic chemists to focus on developing more convenient methods for the synthesis of b-aminoketones. Recent achievements in the efficient construction of these molecules include the development of various catalysts, such as Lewis acid catalysts [17], Bronsted acid catalysts [18,19], and Lewis base catalysts [20], to facilitate Mannich reactions. For example, scandium triflate, copper triflate, scandium tris(dodecyl sulfate), and scandium tris(dodecanesulfonate) [21].…”
Section: Introductionmentioning
confidence: 99%
“…The regioselectivity was determined by 1 H-NMR spectroscopy and by comparison with the literature NMR values. [44][45][46][47] In general, "anti" selectivity was observed when ethyl methyl ketone was used.…”
Section: )mentioning
confidence: 99%