Brønsted Acid-Controlled [3+ 2] Coupling Reaction of Quinone Monoacetals with Alkene Nucleophiles: A Catalytic System of Perfluorinated Acids and Hydrogen Bond …

Y Hu, T Kamitanaka, Y Mishima, T Dohi…

文献索引：Hu, Yinjun; Kamitanaka, Tohru; Mishima, Yusuke; Dohi, Toshifumi; Kita, Yasuyuki Journal of Organic Chemistry, 2013 , vol. 78, # 11 p. 5530 - 5543

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被引用次数: 12

摘要

We have developed an efficient Brønsted acid-controlled strategy for the [3+ 2] coupling reaction of quinone monoacetals (QMAs) with nucleophilic alkenes, which is triggered by the particular use of a specific acid promoter, perfluorinated acid, and a solvent, fluoroalcohol. This new coupling reaction smoothly proceeded with high regiospecificity in regard with QMAs for introducing π-nucleophiles to only the carbon α to the carbonyl group, thereby ...