ArticleNature communications2024
Organocatalytic desymmetrization provides access to planar chiral [2.2]paracyclophanes.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 39 citations in OpenAlex.
- Atroposelective Construction of Axially Chiral Tetraarylethenes Via NHC-Catalyzed Desymmetrization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Catalytic Enantioselective Construction of Planar Chiral Heterocyclic [2.2]Paracyclophanes Enabled by Copper-Catalyzed Desymmetric Azide-Alkyne Cycloaddition.Nature communications · 2026Article
- Carbene-catalyzed double esterification enables enantioselective conformational self-locking of pillar[5]arenes.Nature communications · 2026Article
- Construction of remote dual stereocenters by electrochemical cobalt-catalyzed enantioselective desymmetrization.Nature communications · 2026Article
- Carbene-catalytic enantioselective synthesis of chiral macrocycles.Chemical science · 2025Review
- Enantioselective Desymmetrization by Chiral Bifunctional H-Bonding Organocatalysts.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Stereocontrolled Construction of Multi-Chiral [2.2]Paracyclophanes via Cobaltaphotoredox Dual Catalysis.ACS catalysis · 2025Article
- Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes.Nature communications · 2025Article
- Construction of planar chiral [2,2]paracyclophanes via photoinduced cobalt-catalyzed desymmetric addition.Nature communications · 2025Article
- Organocatalytic desymmetrization provides access to planar chiral [2.2]paracyclophanes.Nature communications · 2024Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Planar chiral [2.2]paracyclophanes consist of two functionalized benzene rings connected by two ethylene bridges. These organic compounds have a wide range of applications in asymmetric synthesis, as both ligands and catalysts, and in materials science, as polymers, energy materials and dyes. However, these molecules can only be accessed by enantiomer separation via (a) time-consuming chiral separations and (b) kinetic resolution approaches, often with a limited substrate scope, yielding both enantiomers. Here, we report a simple, efficient, metal-free protocol for organocatalytic desymmetrization of prochiral diformyl[2.2]paracyclophanes. Our detailed experimental mechanistic study highlights differences in the origin of enantiocontrol of pseudo-para and pseudo-gem diformyl derivatives in NHC catalyzed desymmetrizations based on whether a key Breslow intermediate is irreversibly or reversibly formed in this process. This gram-scale reaction enables a wide range of follow-up derivatizations of carbonyl groups, producing various enantiomerically pure planar chiral [2.2]paracyclophane derivatives, thereby underscoring the potential of this method.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.