NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines

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. Addit...

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Main Authors: Wu, Shuquan, Liu, Changyi, Luo, Guoyong, Jin, Zhichao, Zheng, Pengcheng, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2023
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Online Access:https://hdl.handle.net/10356/170458
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Institution: Nanyang Technological University
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spelling sg-ntu-dr.10356-1704582023-09-12T07:16:48Z NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines Wu, Shuquan Liu, Changyi Luo, Guoyong Jin, Zhichao Zheng, Pengcheng Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Chemoselectivity Dihydroquinolines 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. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) Nanyang Technological University We acknowledge financial support from the National Natural Science Foundation of China (21772029, 21801051 and 21807019), National Key Technologies R&D Program (2014BAD23B01), The 10 Talent Plan (Shicengci) of Guizhou Province([2016]5649), the Natural Science Foundation of Guizhou Province([2018]2802), Guizhou University, the Guizhou Province First-Class Disciplines Project (Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008, the Natural Science Foundation of Guizhou University (GZU[2017]35), the Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University (2018GDGP0101). Singapore National Research Foundation (NRF-NRFI2016-06), the Ministry of Education of Singapore (MOE2013-T2-2-003; MOE2016-T2-1-032; RG108/16), A*STAR Individual Research Grant (A1783c0008), Nanyang Research Award Grant, and Nanyang Technological University. 2023-09-12T07:16:48Z 2023-09-12T07:16:48Z 2019 Journal 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, 131(51), 18581-18584. https://dx.doi.org/10.1002/ange.201909479 0044-8249 https://hdl.handle.net/10356/170458 10.1002/ange.201909479 51 131 18581 18584 en MOE2013-T2-2-003 MOE2016-T2-1-032 RG108/16 A1783c0008 Angewandte Chemie © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Chemoselectivity
Dihydroquinolines
spellingShingle Science::Chemistry
Chemoselectivity
Dihydroquinolines
Wu, Shuquan
Liu, Changyi
Luo, Guoyong
Jin, Zhichao
Zheng, Pengcheng
Chi, Robin Yonggui
NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Wu, Shuquan
Liu, Changyi
Luo, Guoyong
Jin, Zhichao
Zheng, Pengcheng
Chi, Robin Yonggui
format Article
author Wu, Shuquan
Liu, Changyi
Luo, Guoyong
Jin, Zhichao
Zheng, Pengcheng
Chi, Robin Yonggui
author_sort Wu, Shuquan
title NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
title_short NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
title_full NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
title_fullStr NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
title_full_unstemmed NHC‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
title_sort nhc‐catalyzed chemoselective reactions of enals and aminobenzaldehydes for access to chiral dihydroquinolines
publishDate 2023
url https://hdl.handle.net/10356/170458
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