2001
DOI: 10.1021/jo0108764
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Conjugate Addition of Amines to α,β-Enones Promoted by CeCl3·7H2O−NaI System Supported in Silica Gel

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Cited by 176 publications
(65 citation statements)
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“…[16] The approach based on the Michael addition of amines to α,β-unsaturated carbonyl compounds affords an efficacious alternative. [17] The drawbacks encountered with this approach, such as basic conditions, [18] acid catalysis [19] or the problem of double-conjugate addition, [20] led us to develop a general synthesis for these β-amino ketone compounds.…”
Section: Resultsmentioning
confidence: 99%
“…[16] The approach based on the Michael addition of amines to α,β-unsaturated carbonyl compounds affords an efficacious alternative. [17] The drawbacks encountered with this approach, such as basic conditions, [18] acid catalysis [19] or the problem of double-conjugate addition, [20] led us to develop a general synthesis for these β-amino ketone compounds.…”
Section: Resultsmentioning
confidence: 99%
“…Cerium(III) is the most commonly used as chloride or nitrate salt itself or supported on silica gel eventually doped by sodium iodide-this type of supported catalyst was developed by Bartoli and Marcantoni [27,28].…”
Section: Introductionmentioning
confidence: 99%
“…However, these reactions require either basic conditions [7] or acidic catalysts [8] which seem to be detrimental to the desired synthesis. In order to overcome some of the disadvantages, a good number of alternative procedures have been reported over the past few years using Yb(OTf) 3 , [9] InCl 3 , [10] CeCl 3 · 7 H 2 O, [11] Bi(NO) 3 [14] LiClO 4 [15] and heterogeneous solid acids, [16] but the need for an environmentally benign and facile protocol still exists. Room temperature ionic liquids are acknowledged as eco-benevolent alternatives to volatile organic solvents and have also other useful properties like very low vapor pressure, wide liquid range, high thermal stability and possess highly conductive solvation ability for a variety of organic substrates and catalysts including Lewis acids and enzymes.…”
mentioning
confidence: 99%