Preparation of Immobilized L‐Prolinamide Via Enzymatic Polymerization of Phenolic L‐Prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction

Qu, Chengke; Zhao, Wei; Zhang, Lei; Cui, Yuanchen

doi:10.1002/chir.22302

Cited by 13 publications

(5 citation statements)

References 45 publications

(59 reference statements)

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“…(3R,4S)-3,4-dihydroxy-4-(4-nitrophenyl)butan-2-one. 1 H and 13 C NMR spectra were in agreement with References [34][35][36]. The enantiomeric excess was determined using chiral HPLC (Chiral AD-H, iPrOH/n-hexane 15/85, flow: 1 mL/min, λ = 254 nm): t R = 23.21 min (anti major), t R = 25.55 min (anti minor), t R = 30.99 min (syn minor), t R = 43.69 min (syn major).…”

Section: A3 Asymmetric Aldol Reaction-general Proceduressupporting

confidence: 88%

Enantiodivergent Aldol Condensation in the Presence of Aziridine/Acid/Water Systems

et al. 2020

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A series of novel chiral imines was synthesized from corresponding aldehydes and 1-(2-aminoalkyl)aziridines with good chemical yields. Such imines were tested as catalysts in the direct asymmetric aldol reaction between aromatic aldehydes and acetone/cyclohexanone in the presence of catalytic amounts of water and an acidic additive. The corresponding aldol products were formed in excellent yields and with very high enantioselectivities (98% and 99% ee, respectively).

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Section: A3 Asymmetric Aldol Reaction-general Proceduressupporting

confidence: 88%

Enantiodivergent Aldol Condensation in the Presence of Aziridine/Acid/Water Systems

et al. 2020

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“…Polymer supported catalyst 124 (10 mol%) used as an organocatalyst for direct asymmetric aldol reaction between 4‐nitrobenzaldehyde and cyclohexanone in water and afforded the corresponding aldol product in 91% yield and anti/syn (89:11) with 87% ee (Scheme ). The polymer supported organocatalyst can recovered and reused for five cycles with retained activity almost same …”

Section: Prolinamide Catalysed Direct Asymmetric Aldol Reactionmentioning

confidence: 99%

“…Catalyst (88) gave the product (85) in 94% yield and anti/syn (84/16) with 79% ee (Scheme 31). [64] Kokotos and co-workers reported a family of dipeptide (90) consisting of proline and tert-butyl ester of amino acids, as well as simple amides of propyl-glycine dipeptide and evaluated for direct asymmetric aldol reaction (Scheme 32). [65] Juaristi and co-workers reported (L)-proline containing dipeptide catalysed direct asymmetric aldol reaction show the improved stereo induction in solvent free conditions.…”

Section: Prolinamide Catalysed Direct Asymmetric Aldol Reactionmentioning

confidence: 99%

“…The polymer supported organocatalyst can recovered and reused for five cycles with retained activity almost same. [90] Yadav and singh described the synthesis of imdidazolium ionic liquids from bromoester of trans-4-hydroxy-(L)-prolinamide and N-methylimidazole and their catalytic activity in direct asymmetric aldol reaction (Scheme 55). [91] (L)-Prolinamide imidazolium hexafluorophosphate ionic liquid (125) (2 mol%) found to be an excellent organocatalyst for asymmetric direct aldol reaction between 4-nitrobenzaldehyde and cyclohexanone using acetic acid (2 mol%) as additive at -15°C in solventfree condition, the aldol product was afforded in excellent yield with diasteromeric ratio (anti/syn; 97:3) and 94% ee of antiproduct.…”

Section: Immobilisation Of Prolinamidementioning

confidence: 99%

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Prolinamide‐Catalysed Asymmetric Organic Transformations

2019

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Proline was reported as an enantioselective organocatalyst for direct asymmetric aldol reaction in the early 1971 s by two independent groups of researchers and the reaction was called the Hajos‐Parrish‐Eder‐ Sauer Wiechert reaction. The breakthrough of enantioselective organocatalysis was demonstrated by List and co‐workers in 2000 for intermolecular aldol reaction between benzaldehydes and ketone using proline as a catalyst. After this report many researchers were applied the proline as a catalyst for other organic transformation. The proline has a carboxylic functional group which can easily convert to the amide and known as prolinamide. Prolinamides were found to be a better catalyst compared to proline in the most of cases. In this review article we are compiling the results of the prolinamides catalyzed asymmetric organic transformation with insight of the mechanism of catalysis.

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“…Phenolic (S)-prolinamide 5 was enzymatically polymerized using horse radish peroxidase (HRP) to give the polymerimmobilized prolinamide 6. 13 6 was then used as a catalyst for the direct aldol reaction of 2 and 3 to give the aldol addition product 4 in a good yield and with high diastereoselectivity (up to dr 6 : 94) (Scheme 2).…”

Section: Polymer-immobilized Chiral Organocatalystsmentioning

confidence: 99%

Polymer-immobilized chiral catalysts

Itsuno

Hassan

2014

RSC Adv.

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This review illustrates the current strategies and potential of polymer-immobilized chiral catalysts for highly enantioselective asymmetric synthesis. Abstract:Polymer immobilization of chiral catalysts has progressed extensively over the past years. Recent intensive development of chiral organocatalysts resulted in the identification of numerous highly active catalysts, which are, however, still far less effective than transition metal catalysts. Separation of relatively large amounts of organocatalysts from the reaction mixture causes problems during product isolation. In the case of chirally modified metal catalysts, recovery of the valuable metal species and suppression of metal leaching are perpetually important requirements in the design of environmentally friendly chemical processes. Various types of chiral organocatalysts and metal catalysts have been immobilized as pendant groups onto the side chains of polymer supports. Another important polymer immobilization technique is the incorporation of a chiral catalyst into its main chain, with several types of chiral catalyst monomers having been copolymerized with achiral monomers for their production.Recently, the synthesis of chiral main-chain polymeric catalysts has progressed extensively. Moreover, many examples of polymer-immobilized catalysts exhibited higher enantioselectivities in comparison to those of the corresponding low-molecular-weight catalyst. The development of these polymer-immobilized chiral

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Preparation of Immobilized L‐Prolinamide Via Enzymatic Polymerization of Phenolic L‐Prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction

Cited by 13 publications

References 45 publications

Enantiodivergent Aldol Condensation in the Presence of Aziridine/Acid/Water Systems

Enantiodivergent Aldol Condensation in the Presence of Aziridine/Acid/Water Systems

Prolinamide‐Catalysed Asymmetric Organic Transformations

Polymer-immobilized chiral catalysts

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