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Ch_322a_5.015 - The Separation of Enantiomers Resolution...

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The Separation of Enantiomers: Resolution Because enantiomers have identical physical properties, they are not separable by simple direct methods such as distillation, chromatography or crystallization. They may be separated in the presence of a chiral influence that introduces diastereomeric relationships . The separation of the enantiomers of a racemic form is called resolution .
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Resolution Scheme R S Racemic Form (identical properties) R R is a resolving agent. It is a single enantiomer (such as R) of a chiral compound. reaction R R S R + Diastereomers (different properties) R R S R separate - R - R pure forms R S The racemic form ( R , S ) is reacted with a single enantiomer ( R ) of a resolving agent to produce diastereomers ( R,R and S , R ) that are separable by physical means. The resolving agent is then removed producing the pure enantiomers R and S .
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Resolving Agents N HO H N H N O = N H H O H H H quinine strychnine N O = N H H O H H H CH 3 O CH 3 O CH 3 O brucine (from Strychnos seeds) (primary alkaloid from various
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