Asymmetric organocatalysis: from proline to highly efficient immobilized organocatalysts

Kucherenko, Alexander S.; Siyutkin, Dmitry E.; Maltsev, Oleg V.; Kochetkov, Sergei V.; Zlotin, Sergei G.

doi:10.1007/s11172-012-0177-4

Cited by 28 publications

(9 citation statements)

References 50 publications

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“…The domino reaction between α , β -enals and hydroxylamines in the presence of the chiral imidazolium ionic liquids has also been reported by Zlotin’s research group (Fig. 9 , Scheme 16 ) [ 39 - 41 ]. The products of this domino reaction are chiral 3-aryl-5-hydroxyisoxazolidines, which are formed by the Michael addition followed by spontaneous intramolecular acetalization.…”

Section: Internal Asymmetric Induction Via Enaminesupporting

confidence: 52%

Asymmetric Michael Addition Mediated by Chiral Ionic Liquids

Suzuki

2018

MROC

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Chiral ionic liquids with a focus on their applications in asymmetric Michael additions and related reactions were reviewed. The examples were classified on the basis of the mode of asymmetric induction (e.g., external induction/non-covalent interaction or internal induction/covalent bond formation), the roles in reactions (as a solvent or catalyst), and their structural features (e.g., imidazolium-based chiral cations, other chiral oniums; proline derivatives). Most of the reactions with high chiral induction are Michael addition of ketones or aldehydes to chalcones or nitrostyrenes where proline-derived chiral ionic liquids catalyze the reaction through enamine/ iminium formation. Many reports demonstrate the recyclability of ionic liquid-tagged pyrrolidines.

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Section: Internal Asymmetric Induction Via Enaminesupporting

confidence: 52%

Asymmetric Michael Addition Mediated by Chiral Ionic Liquids

Suzuki

2018

MROC

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“…Ionic liquids have been applied as useful alternatives to conventional solvents, catalysts or reagents in organic synthesis, due to their particular properties including: (1) chemical and thermal stability, (2) low vapor pressure, (3) controlled miscibility and polarity, (4) high boiling point, (5) nonflammability, (6) excellent solvent power for organic and inorganic compounds, and (7) ability to catalyze a wide range of organic reactions. Among them, protic acidic ionic liquids (AILs) have been extensively utilized as catalysts and reagents in organic synthesis [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

“…Among them, protic acidic ionic liquids (AILs) have been extensively utilized as catalysts and reagents in organic synthesis [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. This class of ionic liquids combine the advantages of both liquid and solid acids.…”

Section: Introductionmentioning

confidence: 99%

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

et al. 2016

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The aim of this work is to introduce a novel and attractive protic acidic ionic liquid as catalyst for organic synthesis. To achieve this aim, N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et 3 N-SO 3 H]HSO 4 } was prepared by reaction of NEt 3 with ClSO 3 H and then with H 2 SO 4 . The novel acidic ionic liquid was identified by Fourier-transform infrared (FT-IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR, and mass spectroscopies. Its catalytic activity was then examined in the cross-aldol condensation reaction of arylaldehydes with cycloalkanones under solvent-free conditions, obtaining a,a 0 -bis(arylidene)cycloalkanones in high yield after short reaction time. Graphical AbstractKeywords Protic acidic ionic liquid Á N,N-Diethyl-N-sulfoethanaminium hydrogen sulfate {[Et 3 N-SO 3 H]HSO 4 } Á a,a 0 -Bis(arylidene)cycloalkanone Á Crossaldol condensation Á Solvent-free & Abdolkarim Zare

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“…Since then, the number of studies referring to the usefulness of organocatalysts especially in the enantio-selective synthesis has increased remarkably, reflecting their growing potential 7 . Proline and imidazolidinones are well-characterized organocatalysts 8 – 10 . In 2021, the Nobel Prize in Chemistry was awarded to Drs MacMillan and List for the development of asymmetric organocatalysts 11 .…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic activity of granaticin and its involvement in bactericidal function

Nishiyama

Enomoto

Nagayasu

et al. 2022

Sci Rep

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We previously discovered that actinorhodin, a benzoisochromanequinone antibiotic produced by Streptomyces coelicolor A3(2), serves as a catalyst facilitating the oxidation of ascorbic acid and cysteine (PNAS 48:17,152, 2014). In the present study, we screened for similar ascorbic acid-oxidizing activity in the culture broth of various Streptomyces spp., and discovered marked activity in the culture broth of Streptomyces vietnamensis. The principle active compound was granaticin, a pigmented antibiotic that is structurally related to actinorhodin. The absence of any metals in the purified granaticin fraction indicated that granaticin was an organocatalyst. Granaticin catalyzed the oxidation of L-ascorbic acid, generating L-dehydroascorbic acid and hydrogen peroxide (H2O2) at a 1:1 stoichiometric ratio, with 15 times higher reactivity than that of actinorhodin at an optimum pH of 7.0. Granaticin also oxidizes sulfhydryl compounds, including L-cysteine and glutathione. Growth inhibitory assays demonstrated that knockout mutants of the catalase gene exhibit high sensitivity to granaticin. The results suggest that the bactericidal activity of granaticin is exerted by the oxidation of sulfhydryl groups of cellular components and the toxicity of H2O2 generated during the oxidation reaction.

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Asymmetric organocatalysis: from proline to highly efficient immobilized organocatalysts

Cited by 28 publications

References 50 publications

Asymmetric Michael Addition Mediated by Chiral Ionic Liquids

Asymmetric Michael Addition Mediated by Chiral Ionic Liquids

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

Organocatalytic activity of granaticin and its involvement in bactericidal function

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