Kinetic resolution of epoxy alcohols with the Sharpless Ti-isopropoxide/tartaric ester complex

Research paper by Karolin Maljutenko, Anne Paju, Ivar Järving, Tõnis Pehk, Margus Lopp

Indexed on: 14 Jun '16Published on: 11 Jun '16Published in: Tetrahedron: Asymmetry


When investigating the Sharpless epoxidation of enol-protected 4-hydroxy-1,2-cyclopentanediones, the ability of the asymmetric Ti(OiPr)4/tartaric ester complex to discriminate between enantiomeric epoxides formed in situ was discovered, leading to the epoxide opening reaction of only one enantiomer. This observation was used in the kinetic resolution of racemic substituted 2,3-epoxy-4-hydroxy-cyclopentanol, to afford enantiomerically enriched epoxyalcohols in good yields and with ees up to 96%.

Graphical abstract 10.1016/j.tetasy.2016.05.007.jpg
Figure 10.1016/j.tetasy.2016.05.007.0.jpg
Figure 10.1016/j.tetasy.2016.05.007.1.jpg
Figure 10.1016/j.tetasy.2016.05.007.2.jpg
Figure 10.1016/j.tetasy.2016.05.007.3.jpg
Figure 10.1016/j.tetasy.2016.05.007.4.jpg
Figure 10.1016/j.tetasy.2016.05.007.5.jpg
Figure 10.1016/j.tetasy.2016.05.007.6.jpg
Figure 10.1016/j.tetasy.2016.05.007.7.jpg
Figure 10.1016/j.tetasy.2016.05.007.8.jpg