850409-61-9

Usage

Uses

Used in Pharmaceutical and Chemical Research:
9-Amino(9-deoxy)epi-cinchonidine trihydrochloride is utilized as a chiral resolving agent for the separation and analysis of enantiomers, which is crucial for the development and quality control of chiral drugs and compounds.
Used in Chromatography:
In the field of chromatography, 9-Amino(9-deoxy)epi-cinchonidine trihydrochloride serves as a chiral stationary phase, enabling the efficient and selective resolution of enantiomeric mixtures.
Used in Asymmetric Synthesis:
As a reactant in asymmetric synthesis, 9-Amino(9-deoxy)epi-cinchonidine trihydrochloride contributes to the production of enantioselective compounds, which are essential in creating biologically active molecules with specific pharmacological properties.
Used in Analytical Chemistry:
9-Amino(9-deoxy)epi-cinchonidine trihydrochloride is employed as a reagent in various analytical techniques to determine the enantiomeric purity of chiral substances, ensuring the accuracy and reliability of analytical results.

Upstream product

• 485-71-2 Cinchonidin 
• 118-10-5 (1S,3R,4S,8S,9S)-9-hydroxy-cinchonane 

Downstream Products

• 890044-38-9 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinu clidin-2-yl)methyl)thiourea 
• 1256245-86-9 C₃₁H₂₆F₆N₄O₂ 
• 1253690-81-1 (S)-((1S,2S,4S,5R)-5-ethylquinuclidin-2-yl)(quinolin-4-yl)methanamine 

Relevant academic research and scientific papers

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.

Catalytic asymmetric cycloetherification via intramolecular oxy-Michael addition of enols

Carbonyl compounds employed as carbon nucleophiles have played a dominant role in synthetic organic chemistry; however, there is very limited use of these compounds as oxygen nucleophiles. In particular, there are only a few reports on the oxy-Michael addition of the enol forms of carbonyl nucleophiles. In this study, we present the asymmetric cycloetherification of enols, which are generated in situ from enone-bearing ketones, using chiral bifunctional organocatalysts bearing amino and squaramide groups. This transformation chemo- and enantioselectively afforded dihydropyran derivatives, which are the core structures of building blocks for synthesizing glycans.

One-Pot Catalytic Enantioselective Synthesis of 2-Pyrazolines

A scalable, one-pot, enantioselective catalytic synthesis of 2-pyrazolines from beta-substituted enones and hydrazines is described. Pivoting on a two-stage catalytic Michael addition/condensation strategy, the use of an aldehyde to generate a suitable hydrazone derivative of the hydrazine was found to be key for curtailing background reactivity and tuning the catalyst-controlled enantioselectivity. The new synthetic method is easy to perform, uses a new and readily prepared cinchona-derived bifunctional catalyst, is broad in scope, and tolerates a range of functionalities with high enantioselectivity (up to >99:1 e.r.). The significant scalability of this methodology was demonstrated with the synthesis of more than 80 grams of a pyrazoline product with 89 % catalyst recovery.

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.

NOVEL PICOLINAMIDE-CINCHONA ORGANOCATALYSTS AND DERIVATIVES

The present application describes a novel type of picolinamide-cinchona organocatalyst that allows for the successful transformation of ketimines to chiral amines with very high enantioselectivities and with the highest TOFs reported for any particular organocatalyst to date. These organocatalysts have also been immobilized to a variety of solid supports, including magneto-nanoparticles.

Resorcinarene sulfonylated cinchona alkaloid amine compd. heterointerface

PROBLEM TO BE SOLVED: To provide a heteroarenesulfonyl cinchona alkaloid amine catalyst which solves the problems about the lowness of steric selectivity/reactivity of each product even if any of many asymmetric organic molecular catalysts used for the control of asymmetric space are used.SOLUTION: The heteroarenesulfonyl cinchona alkaloid amine compound catalyst is obtained by introducing a hetroarylsulfonyl group onto the nitrogen atom of cinchona alkaloid to form an intramolecular hydrogen bond between the amide hydrogen of the sulfonamide and the hetero atom. A method for manufacturing a β-aminocarbonyl compound using the same is also provided.

Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: An organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent

An efficient organocatalytic methodology has been developed to perform the stereoselective addition of 2-carboxythioesters-1,3-dithiane to nitroalkenes. Under mild reaction conditions γ-nitro-β-aryl-α-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon. The reaction products are versatile starting materials for further synthetic transformations; for example, the simultaneous reduction of the nitro group and removal of the dithiane ring was accomplished, allowing the preparation of a GABAB receptor agonist baclofen.

Procedure-controlled enantioselectivity switch in organocatalytic 2-oxazolidinone synthesis

In a novel organocatalytic formal [3 + 2] cycloaddition to afford chiral 2-oxazolidinones, an enantioselectivity switch could be induced by changing the manner of addition of the reactants, even when the reaction components (cinchona-alkaloid-derived aminothiourea catalyst, substrates, and solvent) were the same.

Asymmetric catalytic cycloetherification mediated by bifunctional organocatalysts

Oxacyclic structures such as tetrahydrofuran (THF) rings are commonly found in many bioactive compounds, and this has led to several efforts toward their stereoselective syntheses. However, the process of catalytic asymmetric cycloetherification for their straightforward synthesis has remained a challenge. In this study, we demonstrate a novel asymmetric synthesis method for THF via the catalytic cycloetherification of ε-hydroxy-α,β- unsaturated ketones mediated by cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature.