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Reporting of Classical Resolutions

Synthesis plans containing a classical resolution step have a sequence of steps as shown in the following. [Pg.63]

In step X, a racemic product in the ratio 1 1 is isolated. In step X + 1, a chiral auxiliary is added to produce a diastereomeric salt that preferentially crystallizes out of solution and is isolated. In step X + 2, this salt is exposed to acidic or basic aqueous solution to liberate the free optically pure product that is finally collected. In this kind of resolution, half the mass of racemic product collected in step X is destined for waste. Therefore, the percent reaction yield for step X + 1 should be less than or equal to 50%. The reaction yields for steps X and X + 2 can be as high as 100%. The problem is that papers will report the percent yield for step 2 with a fraction that exceeds 50%. How can this be What authors have done is the following sleight of hand. The percent yield they report is not with respect to the starting mass of racemic mixture, but with respect to half its mass, that is, the half that will eventually be collected in step X + 2, assuming no losses along the way. Again, chemists have an [Pg.63]


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