Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/155083
Title: Carbene-catalyzed enantioselective aromatic N-nucleophilic addition of heteroarenes to ketones
Authors: Liu, Yonggui
Luo, Guoyong
Yang, Xing
Jiang, Shichun
Xue, Wei
Chi, Robin Yonggui
Jin, Zhichao
Keywords: Science::Chemistry
Issue Date: 2020
Source: Liu, Y., Luo, G., Yang, X., Jiang, S., Xue, W., Chi, R. Y. & Jin, Z. (2020). Carbene-catalyzed enantioselective aromatic N-nucleophilic addition of heteroarenes to ketones. Angewandte Chemie International Edition, 59(1), 442-448. https://dx.doi.org/10.1002/anie.201912160
Journal: Angewandte Chemie International Edition
Abstract: 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.
URI: https://hdl.handle.net/10356/155083
ISSN: 1433-7851
DOI: 10.1002/anie.201912160
Rights: This is the peer reviewed version of the following article: Liu, Y., Luo, G., Yang, X., Jiang, S., Xue, W., Chi, R. Y. & Jin, Z. (2020). Carbene-catalyzed enantioselective aromatic N-nucleophilic addition of heteroarenes to ketones. Angewandte Chemie International Edition, 59(1), 442-448, which has been published in final form at https://doi.org/10.1002/anie.201912160. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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