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Manganese-catalyzed cyclopropanation of allylic alcohols with sulfones

Author

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  • Ke Yu

    (Donghua University)

  • Qin Nie

    (Donghua University)

  • Qianjin Chen

    (Donghua University)

  • Weiping Liu

    (Donghua University)

Abstract

Cyclopropanes are among the most important structural units in natural products, pharmaceuticals, and agrochemicals. Herein, we report a manganese-catalyzed cyclopropanation of allylic alcohols with sulfones as carbene alternative precursors via a borrowing hydrogen strategy under mild conditions. Various allylic alcohols and arylmethyl trifluoromethyl sulfones work efficiently in this borrowing hydrogen transformation and thereby deliver the corresponding cyclopropylmethanol products in 58% to 99% yields. Importantly, a major benefit of this transformation is that the versatile free alcohol moiety is retained in the resultant products, which can undergo a wide range of downstream transformations to provide access to a series of functional molecules. Mechanistic studies support a sequential reaction mechanism that involves catalytic dehydrogenation, Michael addition, cyclization, and catalytic hydrogenation.

Suggested Citation

  • Ke Yu & Qin Nie & Qianjin Chen & Weiping Liu, 2024. "Manganese-catalyzed cyclopropanation of allylic alcohols with sulfones," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-51188-x
    DOI: 10.1038/s41467-024-51188-x
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