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Recent Advances in Catalytic Desymmetrization for the Synthesis of Axially Chiral Biaryls

Junsoo Moon, Sangji Kim, Sujin Lee, Hyun‐A Cho, Ahreum Kim, Min Kyung Ham, Seung Hyun Kim, Jae-Young Jung, Yongseok Kwon

2024ChemCatChem23 citationsDOIOpen Access PDF

Abstract

Abstract Atropisomeric compounds have been discovered in pharmaceuticals and materials science, and their enantioselective syntheses have gained tremendous attention. Among strategies for catalytic atroposelective synthesis, desymmetrization provides robust and straightforward approaches to axially chiral biaryls. Due to the relative ease of substrate design compared to other atroposelective strategies, desymmetrization has emerged as a pivotal stage for converting fascinating chemistry into its atroposelective counterpart, despite challenges such as the formation of achiral products by subsequent catalytic reactions and the long distance between the reaction site and the stereogenic axis. This review offers a comprehensive overview of recent advancements in atroposelective desymmetrization using chiral organo‐ and metal catalysts, addressing challenges and solutions, and aims to provide insights into future developments in this field.

Topics & Concepts

DesymmetrizationEnantioselective synthesisStereocenterAtropisomerCatalysisChemistryCombinatorial chemistryAxial chiralityOrganocatalysisOrganic chemistryAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySynthesis and Properties of Aromatic Compounds