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Updated: Jun 22, 2025

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

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MeOHとHFIPにおける1,2,4,5-テトラジンとエナミンの反応に関する計算研究

Pengchen Ma1,2, Dennis Svatunek2,3, Zixi Zhu4

  • 1Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China.

Journal of the American Chemical Society
|June 28, 2024
PubMed
まとめ

溶媒の選択は1,2,4,5-テトラジンに対する反応経路を決定する. ヘクサフッロアイソプロパノール (HFIP) は,極性溶媒における典型的なC軸反応とは異なり,新しいメカニズムを通じてN軸サイクロアディションを促進する.

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
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