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Axially chiral compounds asymmetric synthesis and applications
Title
Axially chiral compounds [electronic resource] : asymmetric synthesis and applications / edited by Bin Tan.
ISBN
9783527825172
3527825177
9783527825165
3527825169
3527347127
9783527347124
Published
Newark : John Wiley & Sons, Incorporated, 2021.
Physical Description
1 online resource.
Local Notes
Access is available to the Yale community.
Notes
Description based upon print version of record.
5.2.3 Metal-Catalyzed Enantioselective Synthesis of Axially Chiral Styrene.
Electronic reproduction. Hoboken, N.J. Available via World Wide Web.
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Access restricted by licensing agreement.
Other formats
Print version: Tan, Bin Axially Chiral Compounds Newark : John Wiley & Sons, Incorporated,c2021
Format
Books / Online
Language
English
Added to Catalog
April 04, 2022
Contents
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
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