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Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation

Author

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  • Fangyuan Wang

    (Southern University of Science and Technology)

  • Zongpeng Zhang

    (Southern University of Science and Technology)

  • Yu Chen

    (Southern University of Science and Technology)

  • Virginie Ratovelomanana-Vidal

    (PSL University, Chimie ParisTech, CNRS, Institute1 of Chemistry for Life and Health Sciences, CSB2D team)

  • Peiyuan Yu

    (Southern University of Science and Technology)

  • Gen-Qiang Chen

    (Southern University of Science and Technology)

  • Xumu Zhang

    (Southern University of Science and Technology)

Abstract

Chiral succinimide moieties are ubiquitous in biologically active natural products and pharmaceuticals. Until today, despite the great interest, little success has been made for stereodivergent synthesis of chiral succinimides. Here, we report a general and efficient method for accessing 3,4-disubstituted succinimides through a dynamic kinetic resolution strategy based on asymmetric transfer hydrogenation. The Rh catalyst system exhibit high activities, enantioselectivities, and diastereoselectivities (up to 2000 TON, up to >99% ee, and up to >99:1 dr). Products with syn- and anti-configuration are obtained separately by control of the reaction conditions. For the N-unprotected substrates, both the enol and the imide group can be reduced by control of reaction time and catalyst loading. In addition, the detailed reaction pathway and origin of stereoselectivity are elucidated by control experiments and theoretical calculations. This study offers a straightforward and stereodivergent approach to the valuable enantioenriched succinimides (all 4 stereoisomers) from cheap chemical feedstocks in a single reaction step.

Suggested Citation

  • Fangyuan Wang & Zongpeng Zhang & Yu Chen & Virginie Ratovelomanana-Vidal & Peiyuan Yu & Gen-Qiang Chen & Xumu Zhang, 2022. "Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-35124-5
    DOI: 10.1038/s41467-022-35124-5
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    Cited by:

    1. Fengtian Wu & Yuepeng Wang & Yanfei Zhao & Shaojuan Zeng & Zhenpeng Wang & Minhao Tang & Wei Zeng & Ying Wang & Xiaoqian Chang & Junfeng Xiang & Zongbo Xie & Buxing Han & Zhimin Liu, 2024. "Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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