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Usage

Uses

Used in Asymmetric Synthesis:
N-[3,5-bis(trifluoroMethyl)phenyl]-N'-(8α,9S)-cinchonan-9-ylThiourea is used as a chiral ligand in asymmetric synthesis for various chemical reactions. Its unique structure allows it to facilitate the formation of chiral molecules with high enantioselectivity and efficiency.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[3,5-bis(trifluoroMethyl)phenyl]-N'-(8α,9S)-cinchonan-9-ylThiourea is used as a catalyst in the preparation of chiral molecules and pharmaceutical intermediates. Its ability to promote enantioselective reactions makes it a highly sought-after compound for the synthesis of enantiomerically pure drugs and other bioactive compounds.
Used in Organic Chemistry Research:
N-[3,5-bis(trifluoroMethyl)phenyl]-N'-(8α,9S)-cinchonan-9-ylThiourea is also used in organic chemistry research for the development of new synthetic methods and the study of reaction mechanisms involving chiral ligands and catalysts. Its unique structure and potential applications make it an interesting compound for researchers in the field of organic chemistry.

Upstream product

• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 130-95-0 Quinine 
• 485-71-2 Cinchonidin 
• 850409-61-9 (S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine 
• 118-10-5 cinchonidine 

Relevant academic research and scientific papers

Desymmetrization of gem-diols via water-assisted organocatalytic enantio- And diastereoselective cycloetherification

The first desymmetrization of gem-diols forming chiral hemiketal carbons was accomplished via organocatalytic enantio- and diastereoselective cycloetherification, which afforded optically active tetrahydropyrans containing a chiral hemiketal carbon and tetrasubstituted stereocenters bearing synthetically versatile fluorinated groups. The desymmetrization of silanediols was also demonstrated as an asymmetric route to chiral silicon centers.

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.

Synthesis, antibacterial and anti-MRSA activity, in vivo toxicity and a structure-activity relationship study of a quinoline thiourea

We report the synthesis, antibacterial evaluation of a series of thiourea-containing compounds. 1-(3,5-Bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)-((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea 5, was the most active against a rang

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.

Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts

Chiral spiroketal skeletons are found as core structures in a range of bioactive compounds. These natural compounds and their analogues have attracted much attention in the field of drug discovery. However, methods for their enantioselective construction are limited, and easily available optically active spiroketals are rare. We demonstrate a novel catalytic asymmetric synthesis of spiroketal compounds that proceeds through an intramolecular hemiacetalization/oxy-Michael addition cascade mediated by a bifunctional aminothiourea catalyst. This results in spiroketal structures through the relay formation of contiguous oxacycles, in which multipoint recognition by the catalyst through hydrogen bonding imparts high enantioselectivity. This method offers facile access to spiroketal frameworks bearing an alkyl group at the 2-position, which are prevalent in insect pheromones. Optically active (2S,5S)-chalcogran, a pheromone of the six-spined spruce bark beetle, and an azide derivative could be readily synthesized from the bicyclic reaction product. Around and around: A catalytic asymmetric synthesis of spiroketals through an intramolecular hemiacetalization/oxy-Michael addition cascade with a bifunctional aminothiourea catalyst was developed. This method offers facile access to spiroketal frameworks bearing an alkyl group at the 2-position. Optically active (2S,5S)-chalcogran, a pheromone from the six-spined spruce bark beetle, and a derivative were readily synthesized from the bicyclic reaction product.

Asymmetric Oxy-Michael Addition to γ-Hydroxy-α,β-Unsaturated Carbonyls Using Formaldehyde as an Oxygen-Centered Nucleophile

Formaldehyde was utilized as an oxygen-centered nucleophile in an asymmetric oxy-Michael addition to γ-hydroxy-α,β-unsaturated carbonyl compounds using bifunctional organocatalysts through hemiacetal intermediates. The cyclic acetal product could be further transformed into β-hydroxycarbonyl compounds, useful synthetic intermediates leading to various important target molecules. As such, this method is an example of a novel formal asymmetric hydration of α,β-unsaturated carbonyl compounds.

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 cycloetherifications by bifunctional aminothiourea catalysts: The importance of hydrogen bonding

Chiral oxacyclic frameworks are prevalent in many natural products and bioactive compounds. In addition, a number of them are important synthetic intermediates. Thus, the synthesis of such structures is a significant goal in the field of organic chemistry. However, the development of catalytic asymmetric cycloetherification for the straightforward synthesis of these compounds remains a challenge. In this study, we propose the use of aminothiourea catalysis as an effective way to accomplish such a challenge. The asymmetric synthesis of chiral oxygen heterocycles, including tetrahydrofurans, tetrahydropyrans, and 1,3-dioxolanes, is demonstrated herein using intramolecular oxy-Michael addition mediated by bifunctional aminothiourea catalysts. Georg Thieme Verlag Stuttgart · New York.

Asymmetric indoline synthesis via intramolecular aza-Michael addition mediated by bifunctional organocatalysts

A novel method for the asymmetric synthesis of 2-substituted indolines, employing bifunctional amino(thio)urea catalysts, was developed. The reaction proceeded via an intramolecular aza-Michael addition mediated by activation through hydrogen bonding. The

Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins

A direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20:1 dr) and high enantioselectivity (up to 99:1 er).