Resolution can be used to separate enantiomers
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص1106-1107
2025-08-11
551
Resolution can be used to separate enantiomers
you to resolution as a means of separating enantiomers. Resolution requires an enantiomerically pure resolving agent, which must be a compound from the chiral pool or a simple derivative of that compound. When the Swiss company Cilag wanted one enantiomer of the unusual chiral amino acid in the margin in order to make some potential drug candidates, the chemists there decided the easiest way to get hold of it quickly and in large quantities was to make it in racemic form and then resolve it. It turned out that one of the two enantiomers of the protected derivative below forms a crystalline salt with cheap, readily available (–)-ephedrine, while the other remains in solution. Filtration and treatment with acid to remove the protecting group and protonate the acid gave them a single enantiomer of their target amino acid.
Of course, with resolution, there is a maximum yield of 50% because if you only want one enantiomer, the other is wasted. But there are many cases where you might want both enantiomers. You may need to test them both for biological activity, for example. In that case, resolution is ideal—in the example above the chemists at Cilag could get hold of the other enantiomer of the amino acid just by evaporating the mother liquors from the recrystalliza tion. This is a big advantage of resolution: it lets you get both enantiomers using just one compound from the chiral pool.
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