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Organocatalytic dynamic kinetic resolution of N-arylindole lactams: atroposelective construction of axially chiral amino acids bearing a C-N chiral axis

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Abstract

Organocatalytic dynamic kinetic resolution of configurationally labile cyclic molecules represents one of the most efficient methods for the atroposelective construction of axially chiral molecules bearing a tetra-ortho-substituted chiral axis. Notably, this privileged strategy is limited to constructing a C-C chiral axis. Herein, organocatalytic dynamic kinetic resolution of configurationally labile N-arylindole lactams has been successfully achieved at the first time, allowing for access to a structurally diverse set of axially chiral N-arylindole amino esters with a tetra-ortho-substituted C-N chiral axis in excellent yields and atroposelectivities. In addition to the N-arylindole skeleton, N-aryl thieno[3,2-b]pyrrole, furo[3,2-b]pyrrole, and pyrrolo[2,3-b] pyridine skeletons are also compatible with this transformation. This transition-metal-free facile strategy features a broad substrate scope, mild reaction conditions, easy scale-up and excellent atom economy. Several potentially valuable molecules, such as axially chiral peptides, were efficiently generated from the resulting configurationally stable axially-chiral N-arylindole amino esters, demonstrating the power of this strategy.

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Acknowledgements

This work was support by the National Key Research and Development Program of China (2017YFA0204704), the General Program of Chongqing Natural Science Foundation Project (cstc2020jcyj-msxmX0712), Ningbo Natural Science Foundation (202003N4063), the National Natural Science Foundation of China (21602105, 22174065), and the Natural Science Foundation of Jiangsu Province (BK20171460).

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Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Flexible Electronics & Institute of Advanced Materials, Nanjing Tech University, Nanjing, 211816, China

    Xianfang Hong, Jingcheng Guo, Jinhua Liu, Wei Cao, Chenlong Wei, Ye Zhang & Zhenqian Fu

  2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, China

    Xiaoxiang Zhang

  3. Ningbo Institute, Chongqing Technology innovation Center, Frontiers Science Center for Flexible Electronics (FSCFE), Northwestern Polytechnical University, Xi’an, 710072, China

    Zhenqian Fu

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  1. Xianfang Hong
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  2. Jingcheng Guo
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  3. Jinhua Liu
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  4. Wei Cao
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  5. Chenlong Wei
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Correspondence to Zhenqian Fu.

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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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11426_2021_1209_MOESM1_ESM.pdf

Organocatalytic Dynamic Kinetic Resolution of N-Arylindole Lactams: Atroposelective Construction of Axially Chiral Amino Acids Bearing a C-N Chiral Axis

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Hong, X., Guo, J., Liu, J. et al. Organocatalytic dynamic kinetic resolution of N-arylindole lactams: atroposelective construction of axially chiral amino acids bearing a C-N chiral axis. Sci. China Chem. 65, 905–911 (2022). https://doi.org/10.1007/s11426-021-1209-2

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  • DOI: https://doi.org/10.1007/s11426-021-1209-2

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