Racemic Resolution, also called optical resolution or chiral resolution, is a traditional widely-used process for the separation of racemic compounds into their enantiomers. Despite the dramatic development of enantioselective synthesis optical resolution remains the most cost effective and operationally simplest method in the manufacturing of enantiopure compounds.
The most common process is the conversion of the racemic mixture into a pair of diastereomeric derivatives, which are separated by conventional recrystallization. Once the two diastereomers are separated, they are converted back to the enantiomers by removal of the resolving agent. The resolving agent can often be recovered.
Cinchona Alkaloids are the preferred racemic resolution agents for acids and alcohols via hemiester being widely used in pharmaceutical, agrochemical industry and fine chemical applications.
Sixteen slightly different substituted Cinchona Alkaloid compounds are available, eight belonging to the blue and eight to the red series. In order to isolate for instance the R-isomer simply choose compounds from the RED SERIES and for S-enantiomer from the BLUE SERIES. Due to the slightly different substitution pattern of the sixteen Cinchona alkaloids the enantiomeric excess can be improved easily during a fine screening.
Example: Racemic Resolution Screening Results
Key Features of Cinchona Alkaloids
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- are the preferred racemic resolution agents for acids and alcohols via hemiester
- are widely used in pharmaceutical, agrochemical industry and fine chemical applications
- 16 slightly different substituted Cinchona alkaloids form easily diastereomeric salts
- 2 pairs of pseudoenantiomers (8 compounds, each with the same stereochemistry)
- enables the resolution of both enantiomers (R) and (S)
- resolution of the more soluble salt by substitution with the pseudoenantiomer is feasible
- process development is fast and easy
- available in multi ton scale
- soluble in a wide range of organic solvents and aqueous solutions
- recyclable and therefore cost-efficient
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