From α-keto acids to nitrile oxides enabled by copper nitrate: a facile access to fused isoxazolines

文献情報

出版日 2021-12-10

DOI 10.1039/D1QO01574E

インパクトファクター 5.281

著者

Yuping Zhu, Tianqi Liu, Bingxin Liu, Houguang Shi, Qitao Tan

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要旨

α-Keto acids were unprecedentedly employed as novel precursors of nitrile oxides on treatment with copper nitrate, which reacted with maleimides via [3 + 2] dipolar cycloaddition leading to pharmacologically interesting fused isoxazolines. This approach offers a unique strategy and complementary method for the convenient generation of alkyl substituted nitrile oxides, compared with previously reported copper nitrate-mediated alkenes or alkynes transformations. Different from the well-documented decarboxylation or decarbonylation of α-keto acids, the mechanistic studies revealed that α-keto acids went through a novel carbon–carbon bond cleavage resulting in the key gem-dinitroalkane intermediates, which were further transformed to nitrile oxides for the following 1,3-dipolar cycloadditions.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

From α-keto acids to nitrile oxides enabled by copper nitrate: a facile access to fused isoxazolines

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