Metal(II) d-Tartarates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles

Article abstract of DOI:10.1246/bcsj.61.1213

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-tartarates as heterogeneous chiral Lewis acid catalysts.The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal(II) d-tartarate, and Zn(II) d-tartarate gave the best enantioselectivity in the respective reactions of 1,2-epoxycyclohexane with 1-butanethiol, aniline, and trimethylsilyl azide to afford the corresponding adducts in 85, 58, and 42 percent ee, respectively.Furthermore, the kinetic resolution of racemic oxiranes with thiols catalyzed by Zn(II) d-tatratate was studied.