345217-87-0

Upstream product

• 130-95-0 quinine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 130-95-0 Quinine 

Downstream Products

• 761434-35-9 9-O-benzyl-6'-hydroxycinchonidine 
• 838821-39-9 9-O-benzylcupreine 
• 1451154-34-9 9-O-benzyl-10,11-dihydro-11-methylaminoquinine 

Relevant academic research and scientific papers

A flexible strategy for the synthesis of bifunctional 6′-(thio)-urea containing Cinchona alkaloid ammonium salts

A flexible and functional group tolerant synthesis route to access a structurally diverse collection of bifunctional 6′-(thio)-urea containing Cinchona alkaloid-based chiral quaternary ammonium salts has been developed. This route gives access to more than 25 different novel urea- and thiourea-containing ammonium salt derivatives, which were not accessible so far.

Stereoselective cyclopropanations of amino-acid derived enones

Stereoselective cyclopropanation of a series of amino acid-derived enones to afford cyclopropyl keto-esters is reported, using a Michael-induced ring closure. The use of quinine and quinidine ether catalysts in the cyclopropanation step afforded the cyclopropyl keto-esters with high stereoselectivity. Results follow a consistent pattern, with the pseudoenantiomeric catalysts leading to opposite stereoselectivity, allowing for synthesis of either the syn or anti diastereomers.

Highly enantioselective amination of α-substituted α-cyanoacetates with chiral catalysts accessible from both quinine and quinidine

(Chemical Equation Presented) The catalytic construction of nitrogen-substituted quaternary stereocenters is an important and challenging task in asymmetric synthesis. In this paper, we describe the use of 6′-OH-modified cinchona alkaloids that are accessible from either quinine or quinidine for the development of a highly enantioselective amination of α,α-disubstituted carbonyl compounds that is suitable for the creation of nitrogen-substituted quaternary stereocenters in either the R or S configuration.

Enantioselective Ammonium Ylide Mediated One-Pot Synthesis of Highly Substituted γ-Butyrolactones

An ammonium ylide mediated access towards trans-β,γ-disubstituted, all-trans-α,β,γ-trisubstituted, and α,α,β,γ-tetrasubstituted γ-butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and α-bromo carbonyl compounds, γ-butyrolactones were obtained in yields between 32–99% with up to excellent diastereoselectivities (>95:5) via a DABCO-mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R,?4R)-β,γ-disubstituted and (2R,?3R,?4R)-α,β,γ-trisubstituted γ-butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration. (Figure presented.).

Cinchona alkaloid C-2' amino derivatives and preparation method thereof

The invention discloses cinchona alkaloid C-2' amino derivatives and a preparation method thereof and belongs to the technical field of synthesis of cinchona alkaloid and its derivatives. The cinchonaalkaloid C-2' amino derivative has a general structural formula shown in the description. The invention also discloses a preparation method of the cinchona alkaloid C-2' amino derivatives. Through hydroxy protection, redox, C-2' orientational functionalization, acidolysis and reaction with isocyanate, isothiocyanate or sulfonyl chloride, a series of cinchona alkaloid C-2' amino derivatives are obtained. The cinchona alkaloid C-2' amino derivatives have broad application prospects as potential chiral small molecule catalysts or in the various synthesis of drug molecules.

Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines

Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional molecules such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.

Asymmetric Multicomponent Sulfa-Michael/Mannich Cascade Reaction: Synthetic Access to 1,2-Diamino-3-Organosulfur Compounds and 2-Nitro Allylic Amines

A novel catalytic asymmetric three-component intermolecular sulfa-Michael/Mannich cascade reaction has been developed using a chiral multifunctional catalyst. This reaction provides facile access to 1-amino-2-nitro-3-organosulfur compounds bearing three c

Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans

A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with hi

Enantioselective α-hydroxylation of β-keto esters catalyzed by cinchona alkaloid derivatives

A highly efficient α-hydroxylation of β-keto esters catalyzed by cupreidine in the presence of cumyl hydroperoxide (CHP) was achieved. The reaction was applied to a wide variety of β-keto esters to give products in high yields (up to 95%) with excellent enantioselectivities (up to 97% ee). The reaction had been successfully scaled up to a gram quantity and (S)-5-chloro-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate - the important intermediate of Indoxacarb were obtained in 96% yield with 86% ee. The enantiomeric excess could be improved to 99% by crystallization, and this method has prospect of industrial application for its advantages of enantioselectivity, ease of catalyst preparation and reclamation of catalyst. Georg Thieme Verlag Stuttgart. New York.

Organocatalytic sequential Michael reactions: Stereoselective synthesis of multifunctionalized tetrahydroindan derivatives

Multifunctionalized tetrahydroindan derivatives with four stereocenters were constructed via two sequential Michael reactions between cyclic γ,δ-unsaturated-β-ketoester and nitroalkenes initiated with 0.5-2 mol % of cinchona alkaloid based bifunctional organocatalysts and then with 1 equiv of tetramethylguanidine for cyclization. The desired products could be obtained in high yields (up to 99% yield) with excellent enantioselectivities (95-99% ee) as well as diastereoselectivities (up to >99:1 dr) even on a gram scale.(Figure Presented)