Chiral recognition in the coordination sphere of a calcium ion that is coordinated to a simple tartaric acid derivative offers new possibilities for the preparative‐scale resolution of nonbasic compounds. An example of a mixed calcium salt formed upon resolution of racemic carboxylic acids is shown on the right.

A simple preparative method for the enantiomeric enrichment of alcohols is reported. Crystallization of the complexes of alcohols formed with calcium and zinc O,O'-dibenzoyltartrates led to effective resolutions of the alcohols. However, zinc and calcium dibenzoyltartrates are complementary resolving agents upon coordinative resolution of less-hindered alkoxy alcohols. Mixed copper(ii) salts of O,O'-dibenzoyltartaric acid formed with carboxylic acids can also be applied to the resolution of alkoxy alcohols, thereby providing the simultaneous resolution of an alcohol and a carboxylic acid. Zinc dibenzoyltartrate can form coordination compounds with alkoxy alcohols as well as lattice inclusion compounds with simple alcohols as revealed by the four X-ray structures reported here.

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The present paper illustrates the development of an advanced technique in optical resolution. Both of the amphetamine enantiomers can be obtained by a two-step distillation in nearly quantitative yield without any loss of the resolving agent. It is proved that the second-order interactions (H-bond) are sufficient for separation of enantiomers by distillation. 0 1994 Wiley-Liss, Inc.