桤木
Diels-Alder反应
化学
有机化学
生物
植物
催化作用
作者
Brandon B. Fulton,Alexia J. Hartzell,H. V. Rasika Dias,Carl J. Lovely
出处
期刊:Molecules
[MDPI AG]
日期:2024-04-22
卷期号:29 (8): 1902-1902
标识
DOI:10.3390/molecules29081902
摘要
In the course of studying Diels–Alder reactions of 4-vinylimidazoles with N-phenylmaleimide, it was discovered that they engage in cycloaddition at room temperature to give high yields of the initial cycloadduct as a single stereoisomer. In certain cases, the product precipitated out of the reaction mixture and could be isolated by simple filtration, thereby avoiding issues with aromatization observed during chromatographic purification. Given these results, intramolecular variants using doubly activated dienophiles were also investigated at room temperature. Amides underwent cycloaddition at room temperature in modest yields, but the initial adducts were not isolable with Nimid-benzyl-protected systems. Attempts to extend these results to the corresponding esters and hydroxamate were less successful with these substrates only undergoing cycloaddition at elevated temperatures in lower yields. Density functional theory calculations were performed to evaluate the putative transition states for both the inter- and intramolecular variants to rationalize experimental observations.
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