Palladium/Amino Acid Co-catalyzed Atroposelective C-H Olefination to Access Tetra-Ortho-Substituted Atropisomers Featuring 2,2'-Difluoro-1-biaryl Scaffolds

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Drugging the Next Undruggable KRAS Allele-Gly12Asp

Qinheng Zheng et al.

Summary: This paper reports a long-awaited small molecule drug candidate for the treatment of pancreatic cancer, targeting the oncogenic KRAS (G12D) mutant, which is currently incurable.

JOURNAL OF MEDICINAL CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Biaryl Atropisomer Synthesis via a Torsional Strain Promoted Ring-Opening Reaction

Xue Zhang et al.

Summary: Arising from restricted rotation in single bonds due to steric or electronic effects, atropisomerism is a fundamental category for molecules to exhibit their three-dimensional characters, particularly in axially chiral biaryl compounds. Despite the widespread occurrence of axially chiral skeletons in natural products and bioactive molecules, catalytic asymmetric methods for their synthesis face challenges in controlling stereoselectivity for highly sterically hindered variants. However, recent studies have shown successful direct asymmetric synthesis of biaryl atropisomers through transition metal catalysis, offering insights into the activation of substrates and changes in chemoselectivity through torsional strain-promoted ring-opening reactions.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

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Article Chemistry, Medicinal

Discovery of AZD4625, a Covalent Allosteric Inhibitor of the MutantGTPase KRASG12C

Jason G. Kettle et al.

Summary: KRAS is a valuable and challenging drug target in oncology, and a specific mutation has made it druggable. The research introduces a structure-based drug design method and presents AZD4625 as a potential treatment for KRASG12C positive tumors. AZD4625 shows high potency and selectivity as a KRASG12C inhibitor, with favorable clearance and oral bioavailability in humans.

JOURNAL OF MEDICINAL CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

Stereoselective construction of atropisomers featuring a C-N chiral axis

Yong-Jie Wu et al.

Summary: This article comprehensively summarizes the research progress of atropisomeric C-N compounds, with a focus on their synthetic strategies, and provides insights into future advancements.

GREEN SYNTHESIS AND CATALYSIS (2022)

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Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Biaryl Atropisomer Synthesis via a Torsional Strain Promoted Ring-Opening Reaction

Xue Zhang et al.

Summary: This article discusses the catalytic asymmetric synthesis of biaryl atropisomers through ring-opening reactions. The studies show that torsional strain can promote ring-opening reactions and provide an efficient method for the preparation of ortho tetra-substituted biaryl atropisomers with high enantioselectivity.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Enantioselective Arylative Activation of Aromatic C-O Bond

Jintong Zhang et al.

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Physical

Enantioselective Cobalt-Catalyzed Reductive Cross-Coupling for the Synthesis of Axially Chiral Phosphine-Olefin Ligands

Xi Zhang et al.

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ACS CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

Jun Kee Cheng et al.

Summary: Atropisomerism is a stereochemical behavior exhibited by three-dimensional molecules with rotationally restricted sigma bonds, and compounds with atropisomerically chiral properties are increasingly utilized in fields where molecular asymmetry is influential. There is a steady demand for atroposelective synthesis, leading to conceptually novel and streamlined methods for expanding the structural diversity of atropisomers. This review summarizes key achievements in the stereoselective preparation of biaryl, heterobiaryl, and nonbiaryl atropisomers between 2015 and 2020, emphasizing synthetic strategies for each structural class and potential applications of atropochiral targets.

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Sotorasib: First Approval

Hannah A. Blair

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DRUGS (2021)

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Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2-Symmetric Biaryls

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Synthesis of Axially Chiral Styrenes through Pd-Catalyzed Asymmetric C-H Olefination Enabled by an Amino Amide Transient Directing Group

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Enantioselective Cross-Coupling for Axially Chiral Tetra-ortho-Substituted Biaryls and Asymmetric Synthesis of Gossypol

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Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Chiral Transient Directing Groups in Transition-Metal-Catalyzed Enantioselective C-H Bond Functionalization

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A Bulky Chiral N-Heterocyclic Carbene Palladium Catalyst Enables Highly Enantioselective Suzuki-Miyaura Cross-Coupling Reactions for the Synthesis of Biaryl Atropisomers

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Palladium/Amino Acid Co-catalyzed Atroposelective C-H Olefination to Access Tetra-Ortho-Substituted Atropisomers Featuring 2,2'-Difluoro-1-biaryl Scaffolds

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