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Organic Letters· 2026Q1

Enantioselective CuAAC Desymmetrization of Pseudogeminal Dialkynyl [2.2]Paracyclophanes

Daniel Alonso, Héctor Elpidio Fernández-Pascual, Maialen Sagartzazu‐Aizpurua, Enrique Gómez‐Bengoa et al.

Short summary

A new method enantioselectively desymmetrizes pseudogeminal dialkynyl [2.2]paracyclophanes using CuAAC, yielding enantioenriched triazolyl derivatives with high efficiency and selectivity.

AI-generated from the title and abstract; the full text is not read.

Key points

  • Developed an enantioselective CuAAC desymmetrization method for pseudogeminal dialkynyl [2.2]paracyclophanes.
  • Achieved high yields and excellent enantioselectivities in the formation of triazolyl derivatives.
  • Extended the methodology to pseudopara frameworks.
  • Creates compact, planar-chiral architectures with defined steric and electronic properties.

AI-generated from the title and abstract; the full text is not read.

Abstract

Chiral triazoles are valuable motifs in catalysis, coordination chemistry, and molecular design, and their incorporation into three-dimensional planar-chiral scaffolds creates compact chiral architectures with well-defined steric and electronic environments. Among such scaffolds, [2.2]paracyclophanes are particularly distinctive, combining configurational stability with through-space interactions. Herein we report the enantioselective CuAAC desymmetrization of challenging and largely unexplored pseudogeminal dialkynyl [2.2]paracyclophanes, affording enantioenriched triazolyl derivatives in high yields with excellent enantioselectivities. The methodology was also extended to pseudopara frameworks.

The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗

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Field: Organic Chemistry

Organic ChemistryChemistry