Desymmetrization of <i>Pseudo</i> ‐ <i>para</i> Diformyl[2.2]Paracyclophane via Brønsted Acid‐Catalyzed Reductive Amination

Access to planar chiral molecules remains a longstanding challenge in asymmetric synthesis. Enantiopure [2.2]paracyclophanes are particularly attractive due to their broad applications in medicinal chemistry, asymmetric catalysis, and materials science. Herein, we present a highly stereoselective approach for the desymmetrization of prochiral pseudo ‐ para diformyl[2.2]paracyclophanes, enabled by chiral Brønsted acid‐catalyzed reductive amination. This method furnishes planar chiral structures with excellent enantiocontrol and broad substrate scope. Moreover, the resulting products can be readily modified, underscoring the utility of this approach as a versatile platform for the asymmetric synthesis of planar chiral [2.2]paracyclophane derivatives.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2026-04-20
DOI
https://doi.org/10.1002/adsc.70433
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
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article

Desymmetrization of Pseudo ‐ para Diformyl[2.2]Paracyclophane via Brønsted Acid‐Catalyzed Reductive Amination

Martin Kamlar, Ivana Cı́sařová, Vojtěch Dočekal, Ján Veselý et al.
Advanced Synthesis & Catalysis
Synthesis and Properties of Aromatic Compounds
article

Desymmetrization of Pseudo ‐ para Diformyl[2.2]Paracyclophane via Brønsted Acid‐Catalyzed Reductive Amination

Martin Kamlar, Ivana Cı́sařová, Vojtěch Dočekal, Ján Veselý, Sandip Baban Shinde
article en

Abstract

Access to planar chiral molecules remains a longstanding challenge in asymmetric synthesis. Enantiopure [2.2]paracyclophanes are particularly attractive due to their broad applications in medicinal chemistry, asymmetric catalysis, and materials science. Herein, we present a highly stereoselective approach for the desymmetrization of prochiral pseudo ‐ para diformyl[2.2]paracyclophanes, enabled by chiral Brønsted acid‐catalyzed reductive amination. This method furnishes planar chiral structures with excellent enantiocontrol and broad substrate scope. Moreover, the resulting products can be readily modified, underscoring the utility of this approach as a versatile platform for the asymmetric synthesis of planar chiral [2.2]paracyclophane derivatives.

Advanced Synthesis & CatalysisVol. 368(9)
Charles University (CZ)
Openalex Percentile: Top 14%
Synthesis and Properties of Aromatic Compounds
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