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Atropisomerism in asymmetric organic synthesis : challenges and applications

Takizawa, Shinobu, editor.

Atropisomerism in asymmetric organic synthesis : challenges and applications

Takizawa, Shinobu, editor.

9783527844258

9783527844234

1 online resource (355 p.)

Description based upon print version of record.

5.4.3 Atropisomeric Synthesis of C O Scaffolds via PTC

Cover -- Title Page -- Copyright -- Contents -- Preface -- About the Editors -- Part I Atroposelective Synthesis -- Chapter 1 Introduction -- 1.1 Molecular Chirality and Atropisomerism -- 1.1.1 Molecular Chirality -- 1.1.2 Axial Chirality and Atropisomerism -- 1.2 Atropisomerism in Asymmetric Organic Synthesis -- 1.3 Atropisomerism: Challenges and Applications -- 1.3.1 Axially Chiral Ligands and Organocatalysts -- 1.3.2 Natural Product Synthesis -- 1.3.3 Atropisomerism in Drug Discovery and Development -- References

Chapter 2 Iron- and Ruthenium-Catalyzed Atroposelective Synthesis of Axially Chiral Compounds -- 2.1 Introduction -- 2.2 Oxidative Homo-coupling of 2-Naphthols to BINOL and Its Derivatives -- 2.3 Oxidative Cross-coupling of 2-Naphthols to Asymmetric BINOLs -- 2.4 Oxidative Spirocyclization of 2-Naphthols -- 2.5 Conclusion -- References -- Chapter 3 Vanadium-Catalyzed Atroposelective Coupling of Arenols and Application in the Synthesis of Polycyclic Heteroaromatics (PHAs) -- 3.1 Introduction -- 3.2 Chiral Vanadium Catalysis in Homo-Coupling of Hydroxycarbazoles

3.3 Chiral Vanadium Catalysis in Hetero-Coupling of Hydroxycarbazole with 2-Naphthols -- 3.4 Enantioselective Synthesis of Oxa[9]helicenes via Chiral Vanadium Complex-Catalyzed Homo-Couplings of Polycyclic Phenols -- 3.5 Enantioselective Synthesis of Oxaza[7]dehydrohelicenes via Chiral Vanadium Complex-Catalyzed Hetero-Couplings of 3-Hydroxycarbazoles and 2-Naphthols -- 3.6 Summary and Conclusion -- References -- Chapter 4 Atroposelective Suzuki-Miyaura Coupling Toward Axially Chiral Biaryls: Mechanistic Insight -- 4.1 Introduction

4.2 Mechanism Insight of SMC Reaction and Enantiodetermining Step -- 4.3 Asymmetric SMC Reaction -- 4.3.1 Examples of Early Studies -- 4.3.2 Consideration of the Asymmetric SMC: Cases Dependent on a Directing Group -- 4.3.3 Consideration of the Asymmetric SMC: Cases Independent of a Directing Group -- 4.4 Conclusion -- References -- Chapter 5 Organocatalytic Enantioselective Formation of Atropisomers -- 5.1 Introduction -- 5.2 Aminocatalysis -- 5.2.1 Atropisomeric Synthesis of C C Biaryls via Aminocatalysis -- 5.2.2 Atropisomeric Synthesis of C C Non-biaryls via Aminocatalysis

5.2.3 Atropisomeric Synthesis of C N Scaffolds via Aminocatalysis -- 5.3 Brønsted Base Catalysis -- 5.3.1 Atropisomeric Synthesis of C C Biaryls and Heterobiaryls via Base Catalysis -- 5.3.2 Atropisomeric Synthesis of C C Non-biaryls via Base Catalysis -- 5.3.3 Atropisomeric Synthesis of C N Scaffolds via Base Catalysis -- 5.3.4 Atropisomeric Synthesis of N N Scaffolds via Base Catalysis -- 5.4 Phase Transfer Catalysis -- 5.4.1 Atropisomeric Synthesis of C C Biaryls, Heterobiaryls, and Non-biaryls via PTC -- 5.4.2 Atropisomeric Synthesis of C N Scaffolds via PTC

Unique overview of the recent synthetic methodologies of the atropisomeric molecules and their numerous practical applications Atropisomerism in Asymmetric Organic Synthesis: Challenges and Applications presents new methodologies, strategies, unique catalysts, and solutions to challenges in the area of oxidative heterocoupling. After a general introduction for the concept of atropisomerism, this book focuses on the recent advances in the atroposelective synthesis of axially chiral compounds and how these advances had a significant impact on several applications in asymmetric catalysis and the synthesis of natural products. The book covers the recent examples of metal-catalyzed (Cu, Fe, Ru, V, etc) and organocatalyzed atroposelective syntheses of axially chiral compounds using diverse approaches, including cross-coupling reactions, ring-opening reactions, formation of new aromatic rings, and desymmetrization via functional group transformation. The impact of these efficient strategies on various applications in asymmetric catalysis, total synthesis of natural products, synthesis of polycyclic heteroaromatics (PHAs), and the drug industry is also addressed. Edited by two highly qualified academics, Atropisomerism in Asymmetric Organic Synthesis explores sample topics including: * Iron- and ruthenium-catalyzed atroposelective synthesis of axially chiral compounds and the catalytic applications of multinuclear zinc complexes with axially chirality * Vanadium-catalyzed atroposelective coupling of arenols and application in the synthesis of polycyclic heteroaromatics PHAs * Mechanisms of atroposelective Suzuki-Miyaura coupling towards axially chiral biaryls and organocatalytic enantioselective formation of atropisomers * Synthesis of atropisomers via enantioselective ring-opening reactions and the impact of axially chiral ligands and catalysts derived from atropisomeric binaphthyl structures * Binaphthyl-based chiral DMAP derivatives in enantioselective transformations and catalytic atroposelective oxidative coupling in natural product synthesis Enabling readers to comprehensively understand the development history, research status, and potential of atropisomeric synthesis, Atropisomerism in Asymmetric Organic Synthesis is an essential, up-to-date reference for researchers and scientists in the field.

John Wiley and Sons

Organic compounds -- Synthesis.

Asymmetric synthesis.

Composés organiques -- Synthèse.

Synthèse asymétrique.

Takizawa, Shinobu,

Salem, Mohamed S. H.,

https://onlinelibrary.wiley.com/doi/book/10.1002/9783527844258