N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments

An N-Heterocyclic carbene (NHC) catalyzed aza-benzoin reaction of benzothiazole-2-carboxaldehydes and N-sulfonylimines is reported for the first time. The target benzothiazole-containing aminoketone products bearing different substituents and substitution patterns can be obtained in good to excellen...

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Main Authors: Li, Wei, Lv, Jie, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
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Online Access:https://hdl.handle.net/10356/155081
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Institution: Nanyang Technological University
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spelling sg-ntu-dr.10356-1550812023-02-28T19:50:32Z N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments Li, Wei Lv, Jie Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry N-Heterocyclic Carbene Organocatalysis An N-Heterocyclic carbene (NHC) catalyzed aza-benzoin reaction of benzothiazole-2-carboxaldehydes and N-sulfonylimines is reported for the first time. The target benzothiazole-containing aminoketone products bearing different substituents and substitution patterns can be obtained in good to excellent yields under mild conditions. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) National Research Foundation (NRF) Accepted version We acknowledge financial support from the National Natural Science Foundation of China (21772029, 21801051, 21961006, 22001173), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Guizhou Province Returned Oversea Student Science and Technology Activity Program [(2014)-2], the Science and Technology Department of Guizhou Province ([2018]2802, [2019]1020, Qiankehejichu-ZK[2021]Key033), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004], the Basic and Applied Research Foundation of Guangdong Province (2019A1515110906), the Guizhou Province First-Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008], Guizhou University of Traditional Chinese Medicine, and Guizhou University (China). Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06), the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG108/16, RG5/19, RG1/18), MOE AcRF Tier 3 Award (MOE2018-T3-1-003), the Agency for Science, Technology and Research (A*STAR) under its A*STAR AME IRG Award (A1783c0008, A1783c0010), GSK-EDB Trust Fund, Nanyang Research Award Grant, Nanyang Technological University. 2022-02-08T05:48:28Z 2022-02-08T05:48:28Z 2021 Journal Article Li, W., Lv, J. & Chi, R. Y. (2021). N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments. Tetrahedron, 94, 132311-. https://dx.doi.org/10.1016/j.tet.2021.132311 0040-4020 https://hdl.handle.net/10356/155081 10.1016/j.tet.2021.132311 2-s2.0-85110291011 94 132311 en NRF-NRFI2016-06 RG108/16 RG5/19 RG1/18 MOE2018-T3-1-003 A1783c0008 A1783c0010 Tetrahedron © 2021 Elsevier Ltd. All rights reserved. This paper was published in Tetrahedron and is made available with permission of Elsevier Ltd. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
N-Heterocyclic Carbene
Organocatalysis
spellingShingle Science::Chemistry
N-Heterocyclic Carbene
Organocatalysis
Li, Wei
Lv, Jie
Chi, Robin Yonggui
N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments
description An N-Heterocyclic carbene (NHC) catalyzed aza-benzoin reaction of benzothiazole-2-carboxaldehydes and N-sulfonylimines is reported for the first time. The target benzothiazole-containing aminoketone products bearing different substituents and substitution patterns can be obtained in good to excellent yields under mild conditions.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Li, Wei
Lv, Jie
Chi, Robin Yonggui
format Article
author Li, Wei
Lv, Jie
Chi, Robin Yonggui
author_sort Li, Wei
title N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments
title_short N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments
title_full N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments
title_fullStr N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments
title_full_unstemmed N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments
title_sort n-heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments
publishDate 2022
url https://hdl.handle.net/10356/155081
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