期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 15, 页码 10054-10061出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01039
关键词
-
资金
- EPSRC [EP/R513155/1, EP/W003724/1]
- University of Bath
A new reaction model relying on different interactions between the nucleophile, electrophile, and catalyst has been proposed to explain the selectivity in the oxazaborolidine-catalyzed Mukaiyama aldol reaction, as the current models based on hydrogen bonding alone are insufficient.
Current models for oxazaborolidine-catalyzed transition-state structures are determined by C-H center dot center dot center dot O-B and C-H center dot center dot center dot O=S formyl hydrogen bonding between the electrophile and catalyst. However, selectivity in the oxazaborolidine-catalyzed Mukaiyama aldol cannot be fully rationalized using these models. Combined density functional theory and noncovalent interaction analyses reveal a new reaction model relying on C-H center dot center dot center dot O, C-H center dot center dot center dot pi, and pi-pi interactions between the nucleophile, electrophile, and catalyst to induce selectivity.
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