The asymmetric ring opening of meso-2, 3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal (II) d-tartrates as heterogeneous chiral Lewis acid catalysts. The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal (II) d-tartrate, and Zn (II) d-tartrate gave the best enantioselectivity in the respective reactions of 1, 2-epoxycyclohexane with 1-butanethiol, aniline, and ...