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dc.contributor.authorLv, Yaen_US
dc.contributor.authorLuo, Guoyongen_US
dc.contributor.authorLiu, Qianen_US
dc.contributor.authorJin, Zhichaoen_US
dc.contributor.authorZhang, Xinglongen_US
dc.contributor.authorChi, Robin Yongguien_US
dc.identifier.citationLv, Y., Luo, G., Liu, Q., Jin, Z., Zhang, X. & Chi, R. Y. (2022). Catalytic atroposelective synthesis of axially chiral benzonitriles via chirality control during bond dissociation and CN group formation. Nature Communications, 13(1), 36-.
dc.description.abstractThe applications of axially chiral benzonitriles and their derivatives remain mostly unexplored due to their synthetic difficulties. Here we disclose an unusual strategy for atroposelective access to benzonitriles via formation of the nitrile unit on biaryl scaffolds pre-installed with stereogenic axes in racemic forms. Our method starts with racemic 2-arylbenzaldehydes and sulfonamides as the substrates and N-heterocyclic carbenes as the organocatalysts to afford axially chiral benzonitriles in good to excellent yields and enantioselectivities. DFT calculations suggest that the loss of p-toluenesulfinate group is both the rate-determining and stereo-determining step. The axial chirality is controlled during the bond dissociation and CN group formation. The reaction features a dynamic kinetic resolution process modulated by both covalent and non-covalent catalytic interactions. The axially chiral benzonitriles from our method can be easily converted to a large set of functional molecules that show promising catalytic activities for chemical syntheses and anti-bacterial activities for plant protections.en_US
dc.description.sponsorshipAgency for Science, Technology and Research (A*STAR)en_US
dc.description.sponsorshipMinistry of Education (MOE)en_US
dc.description.sponsorshipNanyang Technological Universityen_US
dc.description.sponsorshipNational Research Foundation (NRF)en_US
dc.relationMOE2018-T3-1- 003en_US
dc.relation.ispartofNature Communicationsen_US
dc.rights© 2022 The Author(s). 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 licenses/by/4.0/.en_US
dc.titleCatalytic atroposelective synthesis of axially chiral benzonitriles via chirality control during bond dissociation and CN group formationen_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.description.versionPublished versionen_US
dc.subject.keywordsChemical Bondingen_US
dc.description.acknowledgementWe acknowledge financial support from the National Natural Science Foundation of China (21772029, 21801051, 21961006, and 22001173), The ten Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Science and Technology Department of Guizhou Province ([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 (NRFNRFI2016-06) 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. X.Z. acknowledges the support from IHPC, A*STAR, and thanks to the Deputy Chief Executive Research Office (DCERO), A*STAR for a Career Development Fund (CDF Project Number C210812008) for this work. X.Z. acknowledges the partial use of supercomputers in the A*STAR Computational Resource Center (ACRC) for computations performed in this work.en_US
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