Asymmetric oxohydroxylation of α-alkyl enoates with potassium permanganate catalyzed by monocationic quaternary...
Buchler Glossary
Introduction
Buchler is worldwide the leading supplier of Quinine (CAS-No. 130-95-0). It is the most famous compound of the well-known Cinchona Alkaloid family and contains the framework of sophisticated highly efficient chiral organocatalysts. Quinine and its derivatives enables the synthesis of complex chiral compounds in high yield and with remarkable high enantioselectivity. These catalysts are eco-friendly, non-toxic, highly stable and available for reasonable prices. As green catalysts these compounds are widely used in large-scale applications. Please take a look into our free of charge Chiral Catalyst Search Database, containing hundreds of example. Lots of highly efficient enantioselective organocatalysts contain the Quinine framework. Urea and thiourea derivatives of Quinine and other Cinchona Alkaloids are widely used as a chiral catalyst to promote Aldol reaction, Aminations, Cycloadditions, Halogenations, Mannich reaction, Michael Addition, Henry reactions, Epoxidations, Friedel-Crafts reaction etc.
Application
Quinine based Phase Transfer Catalysts (PTC) are often applied to establish the isoxazoline group. For example the key synthetic steps of (S)-Afoxolaner, Flurenaler, Isocycloseram, (S)-Methiozolin, Sorolaner are being catalyzed by Cinchona Alkaloid PTCs. In Addition Desymmetrizations (Briveracetam) of prochiral anhydrides can be achieved easily by Quinine based catalysts with extraordinary high enantioselectivity (> 99 % ee). Moreover the resolution of racemates can be simply carried out using Cinchona Alkaloids or its derivatives as a chiral tool obtaining high values of enantiomeric excess.
Apart from the application in asymmetric synthesis it is also a bitter agent in the beverage industry. Quinine products for the food industry are available as Base, Hydrochloride or Sulfate. Quinine is responsible for the unique bitter taste of beverages such as Tonic Water, Bitter Lemon and many others.
Furthermore Quinine and their salts are used as antimalarial drugs and to treat muscular disorders like leg cramps.
Physical properties
Quinine (CAS-No.: 130-95-0) is a white or almost white, crystalline powder or it consists of fine, colourless needles, being soluble in ethanol, CHCl3 and methanol. The melting point is in the range of 174-179 °C. This compound is not hygroscopic and contains less than 1.0 % water. It could be stored at ambient conditions in well-closed, light-resistant containers.
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