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Asymmetric annulations based on cycloisomerization of cyclopropyl tethered allenyl ketones by bimetallic relay catalysis

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Abstract

The diastereo- and enantioselective tandem cycloisomerization/[4 + 2]-cycloaddition reaction of cyclopropyl tethered allenyl ketones with α,β-unsaturated carbonyl compounds was realized firstly under mild reaction conditions by using bimetallic silver (I)/chiral metal-N,N′-dioxide catalysts, providing a facile and atom-economic route to enantioenriched polysubstituted furopyran derivatives with good results. Possible transition state models were proposed to explain the stereoinduction.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21890723, 22171189) and the Fundamental Research Funds for the Central Universities (YJ201819).

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Authors and Affiliations

  1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China

    Jun He, Wen Liu, Jing Zhang, Ziwei Zhong, Lili Lin & Xiaoming Feng

Authors
  1. Jun He
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  2. Wen Liu
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  3. Jing Zhang
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  4. Ziwei Zhong
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  5. Lili Lin
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  6. Xiaoming Feng
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Corresponding authors

Correspondence to Lili Lin or Xiaoming Feng.

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Conflict of interest The authors declare no conflict of interest.

Additional information

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_2023_1667_MOESM1_ESM.pdf

Asymmetric Annulations Based on Cycloisomerization of Cyclopropyl Tethered Allenyl Ketones by Bimetallic Relay Catalysis

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He, J., Liu, W., Zhang, J. et al. Asymmetric annulations based on cycloisomerization of cyclopropyl tethered allenyl ketones by bimetallic relay catalysis. Sci. China Chem. 66, 2803–2809 (2023). https://doi.org/10.1007/s11426-023-1667-9

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  • DOI: https://doi.org/10.1007/s11426-023-1667-9

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