Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/137827
Title: NHC-catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
Authors: Wu, Shuquan
Liu, Changyi
Luo, Guoyong
Jin, Zhichao
Zheng, Pengcheng
Chi, Robin Yonggui
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2019
Source: Wu, S., Liu, C., Luo, G., Jin, Z., Zheng, P., & Chi, R. Y. (2019). NHC-catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines. Angewandte Chemie International Edition, 58(51), 18410-18413. doi:10.1002/anie.201909479
Journal: Angewandte Chemie International Edition
Abstract: An N-heterocyclic carbene (NHC)-catalyzed reaction between α-bromoenals and 2-aminoaldehydes has been developed. Key steps include chemoselective reaction of the NHC catalyst with one of the aldehyde substrates (the bromoenal) to eventually generate an α,β-unsaturated acylazolium intermediate. Addition of the nitrogen atom of aminoaldehyde to the unsaturated azolium ester intermediate followed by intramolecular aldol reaction, β-lactone formation, and decarboxylation leads to chiral dihydroquinolines with high optical purity. The dihydroquinoline products, which are quickly prepared by using this method, can be readily transformed into a diverse set of functional molecules such as pyridines and chiral piperidines.
URI: https://hdl.handle.net/10356/137827
ISSN: 1433-7851
DOI: 10.1002/anie.201909479
Rights: This is the peer reviewed version of the following article: Wu, S., Liu, C., Luo, G., Jin, Z., Zheng, P., & Chi, R. Y. (2019). NHC-catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines. Angewandte Chemie International Edition, 58(51), 18410-18413, which has been published in final form at https://doi.org/10.1002/anie.201909479. 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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