One way of resolving the alcohol by formation of diastereomers is to react it with phthalic anhydride to give a product containing an acid. This can then be resolved by diastereomer formation with a suitable, enantiomerically pure amine, and the enantiomerically pure alcohol regenerated by treatment of the resolved acid with sodium hydroxide to cleave the ester bond.
Two procedures for the kinetic resolution of alkenes are discussed in the text, the Sharpless epoxidation methodology, and asymmetric hydrogenation. Since the compound to be resolved in this case is an allylic alcohol, either of these methods should be suitable.
For details on how this compound was resolved by Shapless epoxidation
methodology see: K.B. Sharpless, C.H. Behrens, T. Katsuki, A.W.M. Lee,
V.S. Martin, M. Takatani, S.M. Viti, F.J. Walker, and S.S. Woodard; Pure
Appl. Chem., 1983, 55, 589-604.
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