期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 38, 页码 8987-8991出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901563
关键词
asymmetric reactions; density functional calculations; Diels-Alder reaction; in situ XAS; iron
资金
- JST (Japan)
- MEXT (Japan) [18H04253, 17KT0006, 15H03809]
- Grants-in-Aid for Scientific Research [15H03809, 17KT0006, 18H04253] Funding Source: KAKEN
The development and use of a multiple-activation catalyst with ion-paired Lewis acid and Bronsted acid in an asymmetric aza-Diels-Alder reaction of simple dienes (non-Danishefsky-type electron-rich dienes) was achieved by utilizing the [FeBr2](+)[FeBr4](-) combination prepared in situ from FeBr3 and chiral phosphoric acid. Synergistic effects of the highly active ion-paired Lewis acid [FeBr2](+)[FeBr4](-) and a chiral Bronsted acid are important for promoting the reaction with high turnover frequency and high enantioselectivity. The multiple-activation catalyst system was confirmed using synchrotron-based X-ray absorption fine structure measurements, and theoretical studies. This study reveals that the developed catalyst promoted the reaction not only by the interaction offered by the ion-paired Lewis acid and the Bronsted acid but also noncovalent interactions.
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