852913-16-7

Usage

Uses

Used in Pharmaceutical Industry:
Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl)phenylthiourea is used as a chiral organocatalyst for the enantioselective synthesis of pharmaceutical compounds. Its ability to induce high stereoselectivity in chemical reactions allows for the production of enantiomerically pure compounds, which is crucial for the development of effective and safe drugs.
Used in Chemical Synthesis:
Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl)phenylthiourea is used as a catalyst in the synthesis of various organic compounds, including:
1. Stereoselective diaryl(nitro)butanone via enantioselective Michael addition of nitromethane to chalcones.
2. Enantioselective β-amino acids via asymmetric Mannich reaction of malonates with aryl and alkyl imines.
3. The synthesis of 3-indolylmethanamines by the reaction of indoles with imines via asymmetric Friedel-Crafts reaction.
4. The enantioselective conjugate addition of active methylene compounds to enones to obtain the corresponding addition products.
These applications highlight the versatility of Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl)phenylthiourea as a catalyst in various organic reactions, contributing to the advancement of chemical synthesis and the development of new compounds with potential applications in various industries.

Upstream product

• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 168778-61-8 (8S,9S)-9-azido-(9-deoxy)epiquinine 
• 130-95-0 Quinine 
• 17356-08-0 thiourea 
• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 249731-47-3 9-mesylquinine 
• 130-95-0 quinine 
• 1381884-75-8 (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanamine 
• 189309-10-2 (8α, 9S)-9-amine-6'-methoxycinchonan 

Relevant academic research and scientific papers

Access to Chiral Polycyclic 1,4-Dihydropyridines via Organocatalytic Formal [3 + 3] Annulation of 2-(1-Alkynyl)-2-alken-1-ones with 3-Aminobenzofurans

A rational designed tandem reaction of 2-(1-alkynyl)-2-alken-1-ones with 3-aminobenzofurans enabled by a chiral bifunctional catalyst is described, affording biologically significant polycyclic 1,4-dihydropyridines in moderate to good yields (43-82%) with good to excellent enantioselectivities (83-99%). This formal [3 + 3] annulation reaction reveals good practicality when conducted on a gram scale, and the cycloadduct has the capability for further elaborations.

Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α-Aminomaleimides to β-Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid

Maleimides are often used as electrophiles in conventional reactions; however, their application as nucleophiles is limited to only a few reactions, and reactions utilizing α-aminomaleimides as asymmetric Michael donors have not been reported to date. Thus, in this work, asymmetric Michael addition of α-aminomaleimides as Michael donors to β-nitrostyrenes was conducted for the first time using an organocatalyst derived from a Cinchona alkaloid. Density functional theory investigations were crucial to improve the enantioselectivity of the adduct.

Highly enantioselective aza-henry reaction of ketimines catalyzed by a chiral bifunctional thiourea-tertiary amine derived from quinine

We have developed a highly enantioselective aza-Henry reaction of aryl α-ketoester-derived N-Ts ketimines with a wide range of substrate scope by a simpler bifunctional thiourea-tertiary amine catalyst derived from quinine. A variety of ketimines were investigated and corresponding products were obtained in excellent yields (up to 99% yield) with excellent enatioselectivities (up to 99% ee).

Asymmetric Cycloetherification by Bifunctional Organocatalyst

Attempts to obtain enantiomerically enriched tetrahydrofuran derivatives via an intramolecular oxy -Michael addition reaction of ?-hydroxyenone is discussed. Despite previous difficulties associated with the asymmetric induction of this reaction, which can proceed even without a catalyst, a highly efficient asymmetric induction was realized using a bifunctional organocatalyst derived from a cinchona alkaloid. The reaction could be extended to ζ-hydroxyenone to yield an optically active tetrahydropyran derivative with a high ee. In these reactions, it is important for the gentle acidic and basic sites in the bifunctional organocatalyst to be arranged properly within the molecular skeleton of the catalyst. The high performance asymmetric induction relied on the affinity of the catalyst for the substrate, which played an important role. A disubstituted tetrahydropyran synthesis could be effectively performed via kinetic resolution using ζ-hydroxyenone containing a secondary alcohol moiety using a chiral phosphoric acid catalyst.

Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids

The catalytic asymmetric α-functionalization of prochiral barbituric acids, a subtype of pseudosymmetric 1,3-diamides, to yield the corresponding 5,5-disubstituted (quaternary) derivatives remains essentially unsolved. In this study 2-alkylthio-4,6-dioxopirimidines are designed as key 1,3-diamide surrogates that perform exceedingly in amine-squaramide catalyzed C-C bond forming reactions with vinyl ketones or Morita-Baylis-Hillmann-type allyl bromides as electrophiles. Mild acid hydrolysis of adducts affords barbituric acid derivatives with an in-ring quaternary carbon in unprecedented enantioselectivity, offering valuable materials for biological evaluations.

Solvent-free enantioselective conjugate addition and bioactivities of nitromethane to Chalcone containing pyridine

A series of chiral thioureas derived from quinine were tested as catalysts in the enantioselective Michael additions of nitromethane to α,β-unsaturated ketones containing pyridine. The best results were obtained with the bifunctional catalyst prepared from 3,5-di(trifluoromethyl)-aniline under solvent-free conditions. This thiourea promoted the reaction with high enantioselectivities and chemical yields for aryl ketones. The origins of enantioselectivity were further investigated via experiment and computation. Meanwhile, the products from our reaction showed potent antibacterial activities against rice bacterial leaf blight, with the S-enantiomer performing much better than the R-enantiomer. Given the promising bioactivity of this class of molecules, our work is expected to offer important applications in developing future generations for drug design.

Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes

An enantioselective synthesis of ent-[3]-ladderanol is presented. The ladderanes are an interesting class of molecules for their unique structure of fused cyclobutane rings as well as their perceived biological function of organism protection. The route h

Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

Intramolecular chirality transfer [2 + 2] cycloaddition of enantiomerically enriched allenoates and alkenes is presented. The use of a chiral catalyst was found to be critical to achieve high levels of diastereoselectivity compared to use of an achiral catalyst. The method developed leads to highly substituted cyclobutanes that would be difficult to prepare by alternative methods.

ASYMMETRIC SYNTHESIS OF FUNAPIDE

This invention is directed to asymmetric synthesis of funapide, which is useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.

Stereoselective glycosylation of 2-nitrogalactals catalyzed by a bifunctional organocatalyst

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.