Chiral zinc(II) and copper(II)-catalyzed asymmetric ring-opening reactions of meso-epoxides with aniline and indole derivatives |
| |
Authors: | Masaya Kokubo |
| |
Institution: | Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
| |
Abstract: | The ring-opening reactions of meso-epoxides with aniline and indole derivatives proceeded smoothly in water in the presence of Zn(II) and Cu(II) surfactant-type catalysts to afford the corresponding products in moderate to high yields with good to excellent enantioselectivities. Opposite enantiomers were obtained by using Sc(III) and Zn(II) or Cu(II) with the same chiral ligand. Crystal structures of these catalysts may explain the reversal of the enantioselectivity. Some reactions were also tested in dichloromethane (DCM), and it was revealed that the reactions proceeded faster in water than in DCM. Finally, several non-linear effect experiments suggested unique structure of these chiral catalysts. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|