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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
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, 131(51), 18581-18584.
Project: MOE2013-T2-2-003
Journal: Angewandte Chemie
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.
ISSN: 0044-8249
DOI: 10.1002/ange.201909479
Schools: School of Physical and Mathematical Sciences 
Rights: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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