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

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

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...

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Bibliographic Details
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: Journal Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Activationof Aromatic Nitrogen
Acylazolium
Online Access:https://hdl.handle.net/10356/155083
Description
Summary: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.

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