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Synlett
DOI: 10.1055/a-2741-9190
Letter

Asymmetric intramolecular C-H insertion of N-tosyl diazoimine intermediate from triazole derivative by axially chiral dirhodium(II) carboxylate complex

Authors

  • Wenjie Lu

    1   Institute for Chemical Research, Kyoto University, Kyoto, Japan (Ringgold ID: RIN12918)

  • Takuya Murai

    1   Institute for Chemical Research, Kyoto University, Kyoto, Japan (Ringgold ID: RIN12918)

  • Ryuji Kyan

    2   Laboratory of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Kyoto, Japan (Ringgold ID: RIN12916)

  • Yusuke Kobayashi

    3   Organic chemistry, Kyoto Pharmaceutical University, Kyoto, Japan (Ringgold ID: RIN12916)

  • Takeo Kawabata

    4   Institute for Chemical Research, Kyoto University, Kyoto, Japan

  • Takumi Furuta

    2   Laboratory of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Kyoto, Japan (Ringgold ID: RIN12916)
Further Information
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The asymmetric intramolecular C-H insertion of an in situ generated diazoimine intermediate derived from N-tosyl-1,2,3-triazoles was investigated. Among the chiral paddlewheel dirhodium(II) complexes screened, only C 2 -symmetric-like dirhodium(II) carboxylate complexes bearing axially chiral amino acid derivatives as ligands proved to be effective in asymmetric induction.This catalyst afforded 2,3-disubstituted tetrahydrofurans with reasonable enantioselectivity for the cis-isomer.



Publication History

Received: 02 October 2025

Accepted after revision: 07 November 2025

Accepted Manuscript online:
07 November 2025

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