Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions

Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions

Ferrocene-derived dicarbaldehydes bearing pro-chiral planes are desymmetrized under the catalysis of chiral N-heterocyclic carbene organic catalysts. The reaction features selective activation and reaction of one of the aldehyde moieties of the ferrocene derivative while leaving the other aldehyde u...

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Main Authors: Lv, Xiaokang, Xu, Jun, Sun, Cuiyun, Su, Fen, Cai, Yuanlin, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Planar Chiral Molecule Synthesis
N-Heterocyclic Carbene
Online Access:https://hdl.handle.net/10356/161338
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1613382023-02-28T20:11:38Z Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions Lv, Xiaokang Xu, Jun Sun, Cuiyun Su, Fen Cai, Yuanlin Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Planar Chiral Molecule Synthesis N-Heterocyclic Carbene Ferrocene-derived dicarbaldehydes bearing pro-chiral planes are desymmetrized under the catalysis of chiral N-heterocyclic carbene organic catalysts. The reaction features selective activation and reaction of one of the aldehyde moieties of the ferrocene derivative while leaving the other aldehyde unit untouched. Our reaction affords enantiomerically enriched planar chiral ferrocene products obtained that are amenable for further transformations. Preliminary application studies show encouraging results when our products are explored for catalysis in chemical synthesis and for antimicrobial utilities in pesticide development. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Submitted/Accepted version We acknowledge financial support from the National Natural Science Foundation of China (21961006, 32172459, 22071036), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Science and Technology Department of Guizhou Province ([2019]1020, QiankehejichuZK[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 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) and Competitive Research Program (NRF-CRP22-2019-0002); the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20, RG5/19), MOE AcRF Tier 2 (MOE2019-T2-2- 117), MOE AcRF Tier 3 Award (MOE2018-T3-1-003); Nanyang Research Award Grant, Chair Professorship Grant, Nanyang Technological University. 2022-08-30T05:18:19Z 2022-08-30T05:18:19Z 2022 Journal Article Lv, X., Xu, J., Sun, C., Su, F., Cai, Y., Jin, Z. & Chi, R. Y. (2022). Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions. ACS Catalysis, 12(4), 2706-2713. https://dx.doi.org/10.1021/acscatal.2c00001 2155-5435 https://hdl.handle.net/10356/161338 10.1021/acscatal.2c00001 2-s2.0-85125062550 4 12 2706 2713 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 ACS Catalysis This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.2c00001. 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
Planar Chiral Molecule Synthesis
N-Heterocyclic Carbene
spellingShingle Science::Chemistry
Planar Chiral Molecule Synthesis
N-Heterocyclic Carbene
Lv, Xiaokang
Xu, Jun
Sun, Cuiyun
Su, Fen
Cai, Yuanlin
Jin, Zhichao
Chi, Robin Yonggui
Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
description Ferrocene-derived dicarbaldehydes bearing pro-chiral planes are desymmetrized under the catalysis of chiral N-heterocyclic carbene organic catalysts. The reaction features selective activation and reaction of one of the aldehyde moieties of the ferrocene derivative while leaving the other aldehyde unit untouched. Our reaction affords enantiomerically enriched planar chiral ferrocene products obtained that are amenable for further transformations. Preliminary application studies show encouraging results when our products are explored for catalysis in chemical synthesis and for antimicrobial utilities in pesticide development.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Lv, Xiaokang
Xu, Jun
Sun, Cuiyun
Su, Fen
Cai, Yuanlin
Jin, Zhichao
Chi, Robin Yonggui
format Article
author Lv, Xiaokang
Xu, Jun
Sun, Cuiyun
Su, Fen
Cai, Yuanlin
Jin, Zhichao
Chi, Robin Yonggui
author_sort Lv, Xiaokang
title Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
title_short Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
title_full Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
title_fullStr Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
title_full_unstemmed Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
title_sort access to planar chiral ferrocenes via n-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
publishDate 2022
url https://hdl.handle.net/10356/161338
_version_ 1759853825504575488

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