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Relevant academic research and scientific papers

Proline-Histidine Dipeptide: A Suitable Template for Generating Ion-Tagged Organocatalysts for the Asymmetric Aldol Reaction

Proline-histidine dipeptide laid the foundation for the construction of three new ion-tagged organocatalysts, utilising the imidazole moiety of histidine for generating the quaternary species. A brief comparative investigation of the catalysts in the enam

Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions

In this study, the novel bifunctional homochiral thiourea-L-prolinamides 1–4, tertiary amino-L-prolinamide 5, and bis-L-prolinamides 6 and 7 were prepared from enantiomerically pure (11R,12R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene 8 and (11S,12S

A chemo-enzymatic oxidation/aldol sequential process directly converts arylbenzyl alcohols and cyclohexanol into chiral β-hydroxy carbonyls

The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation has great significance, in that it is not only environmentally friendly but also overcomes only a single methodological drawback, either in the chemical or biological process. Herein, through the utilization of the bulky steric hindrance of chiral proline derivatives, an integrated laccase and proline as a chemo-enzymatic co-catalyst system is developed. It enables an efficient oxidation/aldol enantioselective sequential reaction to be accomplished, overcoming the mutual deactivation issue. As we present in this study, this one-pot organic transformation, an initial laccase-mediated oxidation of arylbenzyl alcohols and cyclohexanol to form aldehydes and cyclohexanone, followed by a subsequent proline derivative-catalyzed aldol condensation of the in situ generated intermediates, provides various 1,2-diastereoisomeric chiral β-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.

Recyclable Helical Poly(phenyl isocyanide)-Supported l-Proline Catalyst for Direct Asymmetric Aldol Reaction in Brine

Abstract: A novel helical poly(phenyl isocyanide) bearing Boc protected l-proline pendants (poly-1m) was designed and synthesized. Removed the protecting Boc groups on the l-proline pendants led to the formation of helical polymer poly-2m, which showed high optical activity owing to the preferred right-handed helix of polyisocyanide main chain. Optically active helical poly-2m showed excellent catalytic ability on asymmetric aldol reaction. Helical polymer catalysts exhibited enhanced stereoselectivity in aldol reaction compared to small molecule l-proline. Under the optimized aldol reaction condition, the enantiomeric excess (ee) and diastereomeric ratio (dr) values of the aldol reaction product were respectively up to 90% and > 20/1. Moreover, the helical polyisocyanide catalyst Poly-2m can be easily recovered and reused in the aldol reaction for at least five cycles with maintained its activity and stereoselectivity. Graphic Abstract: Enantioselective aldol reaction catalyzed by poly-2m.[Figure not available: see fulltext.]

Natural eutectogels: Sustainable catalytic systems for C-C bond formation reactions

Natural eutectogels were prepared by combining the properties of amino acids with the ones of deep eutectic solvents. The soft materials obtained were fully characterised by determining the gel-sol transition temperatures and analysing the mechanical and

Pro-phe derivatives as organocatalysts in asymmetric aldol reaction

The aldol reaction which is the most important one among the C-C bond forming reactions, is widely used by synthetic organic chemists to obtain β-hydroxycarbonyl compounds which are important starting components for biologically active compounds in optica

Assessing the Recyclability of Supramolecularly Assembled Organocatalytic Species: A Theoretical Insight

Asymmetric organocatalytic synthesis is a powerful tool in organic chemistry to achieve desired stereoisomers in high purity via mild catalytic routes. The immobilization of homogeneous catalytic species onto heterogeneous phases embodies the evolution of asymmetric catalysis, since it allows the recycling of the catalyst for several runs until degradation. Previously reported non-covalent immobilization of proline-based catalysts for aldol reaction onto magnetic nanoparticles functionalized with β-cyclodextrin (MNP-β-CB) demonstrated the viability of the methodology. This paper proposes two new catalyst recycling strategies based on Cucurbit[7]uril (CB[7]) for the aldol reaction and the Robinson annulation. These recycling methodologies are conceptually different. The former relies on the homogeneous encapsulation of the catalyst in cucurbituril, CB[7] ? Cat, and its recycling in the aqueous phase by extraction of the aldol product with organic solvents. The latter relies on the heterogeneous encapsulation of the catalyst as MNP-CB[7] ? Cat2 system and its recycling by magnetic harvesting. Density functional theory (DFT) calculations have been employed to rationalize the thermodynamics of experimental results, and to suggest caveats and plausible improvements in view of a future catalytic design.

L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water

A series of cholesterol and based hydrophobic urea and thiourea compounds were synthesized and successfully used as a cocatalyst for L-proline catalyzed aldol reactions in the presence of water. The anticonfigured products were obtained with good yields (up to 94%), high diastereoselectivities (up to 95:5), and high enantiomeric excesses (up to 93% ee). The successful results for catalytic efficiency of L-proline in the presence of water reveal the importance of the hydrophobic nature of cholesterol and diosgenin parts of thiourea on the reactivity and selectivity in the presence of water.

Asymmetric reactions in water catalyzed by l-proline tethered on thermoresponsive ionic copolymers

L-Proline was covalently tethered on thermoresponsive ionic block copolymers that formed micelles in aqueous solutions. The block copolymers consisted of a poly(N-isopropylacrylamide) (PNIPAAm) segment and an anionic or cationic polymer segment. These cop

Chiral proline sulfonamide bifunctional catalyst and preparation method and application thereof

The invention discloses a novel chiral sulfonamide bifunctional catalyst and a preparation method and application thereof. The catalyst comprises a compound A or a compound B. The molecular structureof the compound A is shown as a formula (I) which is des