期刊
TETRAHEDRON
卷 77, 期 -, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131763
关键词
Epoxide opening; Kinetic resolution; Lewis base catalysis; Silicon tetrachloride; C-H/pi hydrogen bond
资金
- Basic Science Research Program through the National Research Foundation of Korea (NRF) - Ministry of Science ICT [NRF-2020R1F1A1076028]
- GIST Research Institute (GRI) - GIST
This study investigated the factors influencing the enantioselectivity of the chiral Lewis base-catalyzed, SiCl4-promoted kinetic resolution of alpha,beta-dichloro cis-vinyl epoxide, and identified crucial factors determining stereocontrol in the process.
It has been known that the enantioselectivity of the chiral Lewis base-catalyzed, SiCl4-promoted kinetic resolution of alpha,beta-dichloro cis-vinyl epoxide is highly influenced by the configuration of the distal beta-chlorine-bearing stereocenter. In this report, the precise nature of this unusual remote stereocontrol was investigated both experimentally and theoretically. Upon examination of a substrate that has an alkyl group in place of the beta-chlorine substituent, the spatial location of major catalyst-substrate interaction was determined. Subsequently, through computational analysis of transition states, the steric repulsion by the beta-substituents as well as the additional C-H/pi hydrogen bond by the alkyl substituent were proposed as the crucial stereo-determining factors. (C) 2020 Elsevier Ltd. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据