Dicyclohexyl tartrate kinetics

In the kinetic resolution of chiral 1-substituted allylic alcohols, there clearly is benefit to be gained in the choice of tartrate ester used for the reaction. In these reactions, the efficiency of kinetic resolution increases as the size of the tartrate alkyl ester group increases. Data for DMT, DET, and DIPT are summarized below (see Table 6A.8 [6 J), and the trend shown there continues with the use of the crystalline dicyclohexyl and dicyclododecyl tartrates [4],... 

When racemic secondary allylic alcohols 3.17 are subjected to standard Sharpless epoxidation conditions, kinetic resolution takes place [127], By choosing (RJi)- or (5,5)-tartrate, either enantiomer of the epoxyalcohol can be obtained with a maximum yield of 50%, alongside the unreacted allylic alcohol. The ratio of epoxidation rates of the enantiomeric allylic alcohols is usually high enough to obtain both the epoxyalcohol and the unreacted allylic alcohols in high enantiomeric excesses. In some cases, the use of dicyclohexyl- instead of diisopropyl tartrate improves the enantioselectivity. Homoallylic alcohols are also epoxidized, but the selectivities are significantly lower [808]. 

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