Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water

Eyckens, Daniel J.; Brozinski, Hannah L.; Delaney, Joshua P.; Servinis, Linden; Naghashian, Sahar; Henderson, Luke C.

doi:10.1007/s10562-015-1630-4

Cited by 7 publications

(2 citation statements)

References 54 publications

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“…In previous report, ILs acted as alkali catalysts in asymmetric reactions. 45 In the current catalytic system, the essence of the high catalytic activity was the inherent synergistic effect between PIL and organic catalyst built into the PILC nanoparticle.…”

Section: Acs Applied Materials and Interfacesmentioning

confidence: 99%

Nanoparticle Based on Poly(Ionic Liquid) as an Efficient Solid Immobilization Catalyst for Aldol Reaction and Multicomponent Reaction in Water

Jia

et al. 2016

ACS Appl. Mater. Interfaces

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An environmentally friendly nanoparticle-supported catalyst was successfully prepared via in situ ionic complexation between imidazolium-based polymer ionic liquid (PIL) and poly(l-prolinamide-co-MAA). The physical and chemical properties of the obtained nanoparticles were characterized by TEM, FTIR, XPS, and static water contact angle experiments. The surface properties of the nanoparticle were found to significantly affect the catalytic performance. The nanoparticle with PIL outer facilitated the adsorption of reaction substrate in it. As a result, the catalytic system catalyzed the asymmetric Aldol reaction and multicomponent reaction in pure water efficiently. The catalytic system was able to be reused and recycled five times, and with no discernible loss in catalytic activity and enantioselectivity. These findings suggest that nanoparticles based on PIL may provide a new approach for preparing high performance supported catalysts for organic reactions in water. This technology also addresses issues associated with mass transfer in pure water reactions.

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Section: Acs Applied Materials and Interfacesmentioning

confidence: 99%

Nanoparticle Based on Poly(Ionic Liquid) as an Efficient Solid Immobilization Catalyst for Aldol Reaction and Multicomponent Reaction in Water

Jia

et al. 2016

ACS Appl. Mater. Interfaces

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“…[1][2][3][4][5][6][7][8][9] Among several synthetic methods to obtain enantiomer-enriched, γ-nitro carbonyl compounds, asymmetric conjugate addition of carbonyl compounds to nitroalkenes using organocatalysts is one of the most convenient and environmentally benign methodologies. [10][11][12][13][14][15][16][17] Organocatalysis between carbonyl compounds and nitro alkenes has been reported by several research groups; however, due to obstacles faced by most previously reported organocatalysis, such as high catalyst loading or long reaction times, the development of organocatalysts for highly efficient asymmetric conjugate additions of carbonyl compounds to nitroalkenes still remains an area of research interest. Thiourea organocatalysts, which are represented by Takemoto catalysts, are excellent catalysts and are applied to remarkably important asymmetric reactions.…”

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confidence: 99%

Asymmetric Conjugate Additions of Carbonyl Compounds to Nitroalkenes under Solvent-Free Conditions Using Fluorous Diaminomethylenemalononitrile Organocatalyst

Hirashima

Narushima

Kawada

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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The novel fluorous organocatalyst bearing a diaminomethylenemalononitrile motif is prepared. The fluorous organocatalyst efficiently promotes asymmetric conjugate additions of ketones to nitroalkenes and results in high yields of these addition products with excellent enantioselectivities under solvent-free conditions.Key words organocatalyst; fluorous; conjugate addition; solvent-free Chiral γ-nitro carbonyl compounds are significant synthons in organic and medicinal chemistry owing to their easy access to biologically active molecules.1-9) Among several synthetic methods to obtain enantiomer-enriched, γ-nitro carbonyl compounds, asymmetric conjugate addition of carbonyl compounds to nitroalkenes using organocatalysts is one of the most convenient and environmentally benign methodologies. [10][11][12][13][14][15][16][17] Organocatalysis between carbonyl compounds and nitro alkenes has been reported by several research groups; however, due to obstacles faced by most previously reported organocatalysis, such as high catalyst loading or long reaction times, the development of organocatalysts for highly efficient asymmetric conjugate additions of carbonyl compounds to nitroalkenes still remains an area of research interest. Thiourea organocatalysts, which are represented by Takemoto catalysts, are excellent catalysts and are applied to remarkably important asymmetric reactions.18-26) Good organocatalytic activity is seen when a thiourea motif functions as a double hydrogen-bond donor for a nucleophilic substrate. In addition, a squaramide motif as a further double hydrogen-bond donor was reported by Rawal and colleagues, and the squaramide organocatalyst effectively promotes the asymmetric conjugate additions of 1,3-diketones to nitroalkenes. 27) Since the Rawal's report, it has been reported that various organocatalysts with squaramide motifs are useful for several important asymmetric reactions. [28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43] We recently reported the diaminomethylenemalononitrile (DMM) motif as another type of double hydrogen-bond donor, and the DMM-type organocatalysts exhibited excellent asymmetric catalytic activity for several significant asymmetric reactions. [44][45][46][47][48][49][50] Organocatalyst 1 bearing a DMM motif and a cyclic secondary amine unit is a good catalyst for both asymmetric conjugate additions of cyclic ketones to nitroalkenes and direct aldol reactions of aromatic aldehydes with cyclic ketones under solvent-free conditions 45,48) (Fig. 1). On the contrary, asymmetric reactions using organocatalysts with fluorous tags have been reported by several research groups. Almost all of these reports utilize the benefits of fluorous molecules; the recycling of fluorous organocatalysts was achieved via the fluorous solid-phase extraction (FSPE) technique using fluorous silica gel. [73][74][75] We have also reported some fluorous organocatalysts and demonstrated their recyclability. [76][77][78][79][80] It was found that modifying original organocatalysts via add...

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Preparation and characterization of magnetic graphene nanocomposite containing Cu(proline)2 as catalyst for asymmetric aldol reactions

2019

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Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water

Cited by 7 publications

References 54 publications

Nanoparticle Based on Poly(Ionic Liquid) as an Efficient Solid Immobilization Catalyst for Aldol Reaction and Multicomponent Reaction in Water

Nanoparticle Based on Poly(Ionic Liquid) as an Efficient Solid Immobilization Catalyst for Aldol Reaction and Multicomponent Reaction in Water

Asymmetric Conjugate Additions of Carbonyl Compounds to Nitroalkenes under Solvent-Free Conditions Using Fluorous Diaminomethylenemalononitrile Organocatalyst

Preparation and characterization of magnetic graphene nanocomposite containing Cu(proline)2 as catalyst for asymmetric aldol reactions

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