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|Title:||NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines||Authors:||Wu, Shuquan
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. https://dx.doi.org/10.1002/ange.201909479||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.||URI:||https://hdl.handle.net/10356/170458||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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