Metal(II)<i>d</i>-Tartrates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles
作者:Hiroyuki Yamashita
DOI:10.1246/bcsj.61.1213
日期:1988.4
The asymmetricringopening 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
通过使用金属 (II) d-酒石酸盐作为非均相手性路易斯酸催化剂,研究了具有硫醇、苯胺和三甲基甲硅烷基叠氮化物的 meso-2,3-di 取代的环氧乙烷的不对称开环。对映选择性随环氧乙烷、亲核试剂和金属 (II) d-酒石酸盐的组合而变化很大,并且 Zn(II) d-酒石酸盐在 1,2-环氧环己烷与 1-丁硫醇、苯胺、和三甲基甲硅烷基叠氮化物分别以 85%、58% 和 42% ee 提供相应的加合物。此外,研究了由 Zn(II) d-酒石酸盐催化的具有硫醇的外消旋环氧乙烷的动力学拆分。