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Axially chiral compounds : asymmetric synthesis and applications

Tan, Bin (Writes on Chemistry)

Axially chiral compounds : asymmetric synthesis and applications

Tan, Bin (Writes on Chemistry)

9783527825172

9783527825165

Newark : John Wiley & Sons, Incorporated, 2021.

1 online resource (339 pages)

5.2.3 Metal-Catalyzed Enantioselective Synthesis of Axially Chiral Styrene.

Cover -- Title Page -- Contents -- Preface -- Part I Asymmetric Synthesis -- 1 Introduction and Characteristics -- 1.1 Introduction and Classification -- 1.2 Specification of Configuration -- References -- 2 Metal-Catalyzed Asymmetric Synthesis of Biaryl Atropisomers -- 2.1 Introduction -- 2.2 Biaryl Coupling -- 2.2.1 Cross-coupling -- 2.2.2 Other Types of Cross-coupling -- 2.2.3 Oxidative Coupling -- 2.3 Desymmetrization and (Dynamic) Kinetic Resolution via Functional Group Transformation -- 2.3.1 Desymmetrization of Prochiral Biaryls

2.3.2 Kinetic Resolution of Racemic Axially Chiral Biaryls -- 2.3.3 Dynamic Kinetic Resolution of Racemic Axially Chiral Biaryls -- 2.3.4 Ring-opening Reactions -- 2.4 Formation of Aromatic Ring via [2 + 2 + 2] Cycloaddition -- 2.4.1 Cobalt-Catalyzed Enantioselective [2 + 2 + 2] Cycloadditions -- 2.4.2 Rhodium-Catalyzed Enantioselective [2 + 2 + 2] Cycloadditions -- 2.4.3 Iridium-Catalyzed Enantioselective [2 + 2 + 2] Cycloadditions -- 2.5 CH Bond Functionalization -- 2.5.1 Chiral Catalyst-Controlled CH Bond Functionalization -- 2.5.2 Chiral Auxiliary-Induced CH Bond Functionalization

2.5.3 Atroposelective CH Arylation -- 2.6 Summary and Conclusions -- References -- 3 Organocatalytic Asymmetric Synthesis of Biaryl Atropisomers -- 3.1 Introduction -- 3.2 Atroposelective Synthesis of Biaryls by Kinetic Resolution Strategy -- 3.2.1 Conventional Kinetic Resolution -- 3.2.2 Dynamic Kinetic Resolution Strategy -- 3.3 Atroposelective Synthesis of Biaryls by Desymmetrization Strategy -- 3.4 Atroposelective Arene Formation to Access Axially Chiral Biaryls -- 3.4.1 Intramolecular Atroposelective Arene Formation -- 3.4.2 Atroposelective Arene Formation via Intermolecular Annulation

3.5 Atroposelective Synthesis of Biaryls via Direct C-H Arylation Strategy -- 3.5.1 Organocatalytic C-H Arylation by [3,3]-Sigmatropic Rearrangement -- 3.5.2 Atroposelective Arylation Based on Quinone Derivatives -- 3.5.3 Atroposelective Nucleophilic Aromatic Substitution -- 3.6 Conclusion -- References -- 4 Enantioselective Synthesis of Heterobiaryl Atropisomers -- 4.1 Introduction -- 4.2 Atropisomeric Heterobiaryls Featuring Two Six-Membered Rings -- 4.2.1 Functionalization of Heterobiaryls -- 4.2.2 Atroposelective Ring Formation -- 4.3 Atropisomeric Heterobiaryls Featuring a Five-Membered Ring

4.3.1 From Preformed Cyclic Systems -- 4.3.2 Formation of the Heterobiaryl Axis -- 4.3.3 Atroposelective Ring Formations -- 4.4 Atropisomeric Heterobiaryls Featuring Two Five-Membered Rings -- 4.4.1 Functionalization of Heterobiaryls -- 4.4.2 Aromatization of a Bis-heterocycle -- 4.4.3 Atroposelective Ring Formations -- 4.5 Conclusion and Outlook -- References -- 5 Asymmetric Synthesis of Nonbiaryl Atropisomers -- 5.1 Introduction -- 5.2 Styrenes -- 5.2.1 Axially Chiral Styrenes via Point-to-Axial Chirality Transfer -- 5.2.2 Axially Chiral Styrenes Controlled by Chiral Auxiliary

Appearing widely in natural products, biologically active molecules, asymmetric chemistry, and material science, axially chiral motifs constitute the core backbones of the majority of chiral ligands and organocatalysts in asymmetric catalysis. In a new work of particular relevance to synthetic chemists, Axially Chiral Compounds: Asymmetric Synthesis and Applications delivers a clearly structured and authoritative volume covering the classification, characteristics, synthesis, and applications of axial chirality. A must read for every synthetic chemist practicing today, the book follows the development history, research status, and applications of axial chirality. An introductory chapter familiarizes the reader with foundational material before the distinguished authors describe the different classes and the synthesis of axial chiral compounds used in asymmetric synthesis.

John Wiley and Sons

Asymmetric synthesis.

Chirality.

Synthèse asymétrique.

Chiralité.

Asymmetric synthesis

Chirality

Tan, Bin (Writes on Chemistry)

https://onlinelibrary.wiley.com/doi/book/10.1002/9783527825172