Carbene-catalyzed enantioselective aromatic N-nucleophilic addition of heteroarenes to ketones

• Main Authors: Liu, Yonggui, Luo, Guoyong, Yang, Xing, Jiang, Shichun, Xue, Wei, Chi, Robin Yonggui, Jin, Zhichao
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2022
• Subjects: Science::Chemistry; Activationof Aromatic Nitrogen; Acylazolium
• Online Access: https://hdl.handle.net/10356/155083
• Institution: Nanyang Technological University

The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.