Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles

Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles

A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial subs...

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Main Authors: Fan, Guodong, Wang, Qingyun, Xu, Jun, Zheng, Pengcheng, Chi, Robin Yonggui
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2023
Subjects:
Science::Chemistry
Carbohydrate Analysis
Enantioselectivity
Online Access:https://hdl.handle.net/10356/170937
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1709372023-10-13T15:31:44Z Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles Fan, Guodong Wang, Qingyun Xu, Jun Zheng, Pengcheng Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Science::Chemistry Carbohydrate Analysis Enantioselectivity A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial substrates. Mechanistic studies via experiments suggest that our chemoselectivity controls are mostly achieved on the reducing properties of different sited Breslow intermediates. Several side reactions processes and the corresponding side adducts are also studied by high resolution mass spectroscopy analysis. Our method allows for efficient assembly of the furo[2,3-b]pyrrole structural moieties and their analogues widely found in natural products and pharmaceuticals. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Published version The authors acknowledge funding supports from the National Natural Science Foundation of China (21732002, 22061007, P.C.Z; and 22071036, Y.R.C); Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY number (2020)004, Y.R.C]; The 10 Talent Plan (Shicengci) of Guizhou Province ([2016] 5649,Y.R.C); Science and Technology Department of Guizhou Province [Qiankehe-jichu-ZK[2022]zhongdian024, P.C.Z], ([2018]2802, [2019]1020, Y.R.C); Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023, Y.R.C) at Guizhou University; Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06, Y.R.C.) and Competitive Research Program (NRF-CRP22-2019-0002, Y.R.C); Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20, RG5/19, Y.R.C), MOE AcRF Tier 2 (MOE2019-T2-2-117, Y.R.C), and MOE AcRF Tier 3 Award (MOE2018-T3-1-003, Y.R.C); a Nanyang Research Award Grant; and a Chair Professorship Grant, Nanyang Technological University. 2023-10-09T04:39:53Z 2023-10-09T04:39:53Z 2023 Journal Article Fan, G., Wang, Q., Xu, J., Zheng, P. & Chi, R. Y. (2023). Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles. Nature Communications, 14(1), 4243-. https://dx.doi.org/10.1038/s41467-023-39988-z 2041-1723 https://hdl.handle.net/10356/170937 10.1038/s41467-023-39988-z 37454112 2-s2.0-85164756380 1 14 4243 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 Nature Communications © The Author(s) 2023. Open Access. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/ licenses/by/4.0/. 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
Carbohydrate Analysis
Enantioselectivity
spellingShingle Science::Chemistry
Carbohydrate Analysis
Enantioselectivity
Fan, Guodong
Wang, Qingyun
Xu, Jun
Zheng, Pengcheng
Chi, Robin Yonggui
Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
description A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial substrates. Mechanistic studies via experiments suggest that our chemoselectivity controls are mostly achieved on the reducing properties of different sited Breslow intermediates. Several side reactions processes and the corresponding side adducts are also studied by high resolution mass spectroscopy analysis. Our method allows for efficient assembly of the furo[2,3-b]pyrrole structural moieties and their analogues widely found in natural products and pharmaceuticals.
author2 School of Chemistry, Chemical Engineering and Biotechnology
author_facet School of Chemistry, Chemical Engineering and Biotechnology
Fan, Guodong
Wang, Qingyun
Xu, Jun
Zheng, Pengcheng
Chi, Robin Yonggui
format Article
author Fan, Guodong
Wang, Qingyun
Xu, Jun
Zheng, Pengcheng
Chi, Robin Yonggui
author_sort Fan, Guodong
title Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_short Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_full Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_fullStr Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_full_unstemmed Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_sort carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to furo[2,3-b]pyrroles
publishDate 2023
url https://hdl.handle.net/10356/170937
_version_ 1781793726079696896

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