Organocatalysts immobilised onto gold nanoparticles: application in the asymmetric reduction of imines with trichlorosilane

Malkov, Andrei V.; Figlus, Marek; Cooke, Graeme; Caldwell, Stuart T.; Rabani, Gouher; Prestly, Mark R.; Kočovský, Pavel

doi:10.1039/b821391g

Cited by 46 publications

(16 citation statements)

References 42 publications

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“…17 Then, they prepared soluble polymer-supported valine derived organocatalyst, which could be recovered through pouring into the methanol and reused at least ve times without loss of activity. To overcome the separation and recovery difficulties, the common solution is the immobilization of organocatalyst.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe₃O₄

Qian

et al. 2015

RSC Adv.

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Magnetic nano-Fe 3 O 4 -supported organocatalysts were synthesized by anchoring valine-derived formamide onto the surface of Fe 3 O 4 magnetic nanoparticles, which were applied in the asymmetric reduction of imines with trichlorosilane at room temperature in toluene. The high level of yield and enantioselectivity catalyzed by magnetic nano-Fe 3 O 4 -supported organocatalysts was obtained. In the immobilization process, Cu I -catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) "click chemistry" was used as the anchored bridge. The magnetic nanoparticles can simplify the recovery of the organocatalyst and its separation from the reaction system. By an external magnet, the catalyst can be recycled and reused five times without a remarkable activity decline.

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Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe₃O₄

Qian

et al. 2015

RSC Adv.

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“…A third recoverable version of the catalyst was achieved by connecting the valine‐derived formamide Lewis base to gold nanoparticles 14. This methodology allows one both to work in a homogeneous solution and to simplify the recovery of the catalyst and its separation from the product.…”

Section: Discussionmentioning

confidence: 99%

Trichlorosilane‐Mediated Stereoselective Reduction of C=N Bonds

2010

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The reduction of C=N bonds represents a powerful and widely used transformation allowing new nitrogen‐containing stereocenters to be generated. Chiral amino groups are ubiquitous in a variety of bioactive molecules such as alkaloids, natural products, drugs, and medical agents, so the development of a catalytic stereoselective process for the preparation of enantiomerically enriched amines through ketoimine reduction is attracting increasing interest, especially in view of future industrial applications. Great efforts to develop efficient organocatalytic methods to perform enantioselective imine reductions and reductive amination processes have recently been made. In the last few years, trichlorosilane‐mediated reductions have received constantly increasing attention because the potential to generate chiral catalysts for imine reduction simply by coordination of HSiCl3 with a chiral Lewis base has allowed the development of several efficient organocatalytic systems. Here we offer a complete overview of different chiral promoters of stereoselective reductions with trichlorosilane, classified as N‐formyl derivatives, which may be considered historically the first class of compounds developed as chiral activators of trichlorosilane, picolinamide derivatives, and miscellaneous compounds presented in that order.

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“…Catalyst Immobilization on Gold Nanoparticles. 7 Immobilization of butanamide, N-(3,5-dimethylphenyl)-2-(formylmethylamino)-3-methyl-, (2S)-on gold nanoparticles afforded homogeneous catalysts that efficiently transformed aryl ketimines to chiral amines with high enantioselectivity (up to 84% ee). Moreover, precipitation of the catalyst nanoparticles from the reaction mixture is easily achieved with absolute ethanol.…”

Section: Effects Of Solvent and Temperature On Stereoselectivitymentioning

confidence: 99%

Butanamide,N-(3,5-dimethylphenyl)-2-(formylmethylamino)-3-methyl-, (2S)-

Noshi

2014

Encyclopedia of Reagents for Organic Synthesis

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Organocatalysts immobilised onto gold nanoparticles: application in the asymmetric reduction of imines with trichlorosilane

Cited by 46 publications

References 42 publications

Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe₃O₄

Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe₃O₄

Trichlorosilane‐Mediated Stereoselective Reduction of C=N Bonds

Butanamide,N-(3,5-dimethylphenyl)-2-(formylmethylamino)-3-methyl-, (2S)-

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Organocatalysts immobilised onto gold nanoparticles: application in the asymmetric reduction of imines with trichlorosilane

Cited by 46 publications

References 42 publications

Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe3O4

Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe3O4

Trichlorosilane‐Mediated Stereoselective Reduction of C=N Bonds

Butanamide,N-(3,5-dimethylphenyl)-2-(formylmethylamino)-3-methyl-, (2S)-

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Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe₃O₄

Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe₃O₄