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Iodide-Mediated [3 + 2]-Cycloaddition Reaction with N-Tosylaziridines and α,β-Unsaturated Ketones

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    Iodide-Mediated [3 + 2]-Cycloaddition Reaction with N-Tosylaziridines and α,β-Unsaturated Ketones
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    • Yuya Nakagawa
      Yuya Nakagawa
      Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
      More by Yuya Nakagawa
    • Keigo Yamaguchi
      Keigo Yamaguchi
      Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
      More by Keigo Yamaguchi
    • Seijiro Hosokawa*
      Seijiro Hosokawa
      Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
      *Email: [email protected]
      More by Seijiro Hosokawa
      Orcidhttps://orcid.org/0000-0002-8036-532X
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2021, 86, 11, 7787–7796
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    https://doi.org/10.1021/acs.joc.1c00532
    Published May 25, 2021
    Copyright © 2021 American Chemical Society
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    Abstract

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    The [3 + 2]-cycloaddition reaction between N-tosylaziridines and α,β-unsaturated ketones was promoted with lithium iodide. The reaction proceeded under mild conditions to provide N-tosylpyrrolidines. Quaternary carbon-possessing 3,3-disubstituted pyrrolidines including spiro compounds were afforded in high yields. A simple procedure with easy to handle reagents makes this reaction concise. The intramolecular version of this reaction was applied to synthesize tropane skeletons.

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.1c00532.

    • Table of solvent screening results of the reaction using n-Bu4NI (Table S1), NOE correlation of compounds 3m (major isomer) and 7a, X-ray crystallography data of compounds 5 and 7b, and 1H and 13C NMR spectra of compounds (PDF)

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    CCDC 2065283–2065284 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    This article is cited by 3 publications.

    1. Liang Wang, Wei Zhang. Recent Advances on Epoxide‐ and Aziridine‐Based [3+2] Annulations. Chemistry – An Asian Journal 2025, 20 (9) https://doi.org/10.1002/asia.202401936
    2. Siyang Xing, Tingxuan Gao, Changkun Jin, Hongguo Dong, Xueying Shao, Kui Wang, Bolin Zhu. Diastereoselective Access to cis ‐1,4‐Disubstitued Tetrahydro‐ γ ‐carbolines via a [Cp*RhCl 2 ] 2 ‐Catalyzed Formal [3+3]‐Cycloaddition. Advanced Synthesis & Catalysis 2023, 365 (1) , 104-109. https://doi.org/10.1002/adsc.202201062
    3. Jonathon S. Russel. Three-membered ring systems. 2023, 57-77. https://doi.org/10.1016/B978-0-443-18939-5.00007-X
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2021, 86, 11, 7787–7796
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.1c00532
    Published May 25, 2021
    Copyright © 2021 American Chemical Society
    Request reuse permissions

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