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

Abstract

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.

Keywords

C–H insertion - Asymmetric reaction - Paddlewheel dirhodium(II) complex - Triazole - Diazoimine

Publikationsverlauf

Eingereicht: 02. Oktober 2025

Angenommen nach Revision: 07. November 2025

Accepted Manuscript online:
07. November 2025

Artikel online veröffentlicht:
27. November 2025

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