Recent Advances in Axial Chirality Construction by Cycloaddition
Abstract
Axial chirality—arising from restricted rotation around a single bond—is a crucial stereochemical phenomenon first identified by Christie and Kenner in 1922. This motif is widespread in nature, with compounds featuring C–C, C–N, or N–N atropisomeric axes exhibiting significant biological and pharmacological activities. Moreover, axially chiral scaffolds are crucial in asymmetric synthesis, both for organometallic catalysis and organocatalysis. Recent years have seen a surge in research on atroposelective strategies, driven by the challenges of controlling axial stability and conformational dynamics. Among them, cycloaddition reactions are particularly attractive as they allow to generate one ring while setting a stereogenic axis. This review focuses on advances from 2021 to 2026, highlighting cycloaddition reactions that directly generate stereogenic axes (C–C, C–N, N–N, C–B, C–O). It covers diverse cycloaddition types and catalytic systems (including transition metals, chiral phosphoric acids, N-hetereocyclic carbenes), categorizing the findings by reaction type and emphasizing their role in atroposelective synthesis.
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BibTeX
@article{duong2026recent,
title = {{Recent Advances in Axial Chirality Construction by Cycloaddition}},
author = {Dang Khoi Duong and Cyrille Kouklovsky and Valérie Alezra and Aurélien de la Torre},
journal = {Synthesis: Journal of Synthetic Organic Chemistry},
year = {2026},
month = jun,
doi = {10.1055/a-2888-8865},
url = {https://hal.science/hal-05797068v1},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Recent Advances in Axial Chirality Construction by Cycloaddition
AU - Dang Khoi Duong
AU - Cyrille Kouklovsky
AU - Valérie Alezra
AU - Aurélien de la Torre
PY - 2026
DA - 2026/06/10
JO - Synthesis: Journal of Synthetic Organic Chemistry
DO - 10.1055/a-2888-8865
UR - https://hal.science/hal-05797068v1
AB - Axial chirality—arising from restricted rotation around a single bond—is a crucial stereochemical phenomenon first identified by Christie and Kenner in 1922. This motif is widespread in nature, with compounds featuring C–C, C–N, or N–N atropisomeric axes exhibiting significant biological and pharmacological activities. Moreover, axially chiral scaffolds are crucial in asymmetric synthesis, both for organometallic catalysis and organocatalysis. Recent years have seen a surge in research on atroposelective strategies, driven by the challenges of controlling axial stability and conformational dynamics. Among them, cycloaddition reactions are particularly attractive as they allow to generate one ring while setting a stereogenic axis. This review focuses on advances from 2021 to 2026, highlighting cycloaddition reactions that directly generate stereogenic axes (C–C, C–N, N–N, C–B, C–O). It covers diverse cycloaddition types and catalytic systems (including transition metals, chiral phosphoric acids, N-hetereocyclic carbenes), categorizing the findings by reaction type and emphasizing their role in atroposelective synthesis.
SN - 0039-7881
SN - 1437-210X
ER -