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Synthesis and alcoholysis of a-alkylated cyclopentane and cyclohexane fused succinic racemic anhydrides in the presence of chiral bases

Bicyclic succinic anhydrides alkylated at the a-position have been prepared and submitted to alcoholysis in the presence of alkaloid bases. Anhydrides with a cyclopentane fused ring, open only from the less hindered side, generating monoesters of >80% ee, whereas cyclohexane fused anhydrides undergo parallel kinetic resolution, producing both regioisomeric monoesters.

cyclic anhydrides; stereoselective alcoholysis; quinine; kinetic resolution; parallel kinetic resolution

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