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Design, synthesis, and applications of stereospecific 1,3-diene carbonyls

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Abstract

The strategy toward the synthesis of various 1,3-dienals or 1,3-dienones is disclosed between diazo compounds and furans, which features metal-free, additive-free, broad functional group tolerance, and readily accessible starting materials. Notably, this strategy is applicable in both intramolecular and intermolecular protocols. Mechanistic studies suggested that the reactions undergo a cyclopropanation/rearrangement sequence. With an E/E-1,3-dienal, corresponding N-tosylhydrazones were readily prepared and subjected to phenylboronic acid to form a double bond migration product and indoles to construct a five-member ring via [3 + 2] annulation reaction.

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Acknowledgements

This work was supported by the National Natural Science Foundation (21772046, 21931013) and Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University. The authors also thank the Instrumental Analysis Center of Huaqiao University for analysis support.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Institute of Next Generation Matter Transformation, College of Material Sciences & Engineering, Huaqiao University, Xiamen, 361021, China

    Qiang Feng, Shihui Wang, Changqing Rao & Qiuling Song

  2. Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China

    Xingxing Ma & Qiuling Song

  3. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China

    Qiuling Song

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  1. Qiang Feng
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Correspondence to Qiuling Song.

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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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Feng, Q., Wang, S., Ma, X. et al. Design, synthesis, and applications of stereospecific 1,3-diene carbonyls. Sci. China Chem. 65, 912–917 (2022). https://doi.org/10.1007/s11426-021-1204-5

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  • DOI: https://doi.org/10.1007/s11426-021-1204-5

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