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Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction and δ-lactam formation: remote enantioselecitvity control and dynamic kinetic asymmetric transformation

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Abstract

An N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote γ-carbon of cyclopropylcarbaldehydes is disclosed for the first time. Diastereo- and enantiomerically enriched multicyclic δ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation (DYKAT) processes. Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21772029, 21801051, 21961006, 22071036, 82360589, 81360589), 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), 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 (China), and Guizhou University.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, 550025, China

    Jie Lv, Xuling Pan, Zhichao Jin & Yonggui Robin Chi

  2. School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, China

    Jun Xu

  3. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore

    Jun Xu & Yonggui Robin Chi

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  1. Jie Lv
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  2. Jun Xu
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  3. Xuling Pan
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  4. Zhichao Jin
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  5. Yonggui Robin Chi
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Correspondence to Yonggui Robin Chi.

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Conflict of interest The authors declare no conflict of interest.

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Lv, J., Xu, J., Pan, X. et al. Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction and δ-lactam formation: remote enantioselecitvity control and dynamic kinetic asymmetric transformation. Sci. China Chem. 64, 985–990 (2021). https://doi.org/10.1007/s11426-021-9989-1

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  • DOI: https://doi.org/10.1007/s11426-021-9989-1

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