Privileged Chiral Ligands and Catalysts

  • ID: 2180034
  • Book
  • 484 Pages
  • John Wiley and Sons Ltd
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Catalytic asymmetric synthesis has been one of the most active research areas in chemistry (Nobel Prize in 2001). The development of efficient chiral catalysts plays a crucial role in asymmetric catalysis. Although many chiral ligands/catalysts have been developed in the past decades, the most efficient catalysts are derived from a few core structures, called "privileged chiral catalysts". This ultimate "must have" and long awaited reference for every chemist working in the field of asymmetric catalysis starts with the core structure of the catalysts, explaining why a certain ligand or catalyst is so successful. It describes in detail the history, the basic structural characteristics, and the applications of these "privileged catalysts". This novel presentation provides readers with a much deeper insight into the topic and makes it a must–have for organic chemists, catalytic chemists, chemists working with/on organometallics, chemists in industry, and libraries.

From the contents:

∗ BINAP

∗ Bisphosphacycles – From DuPhos and BPE to a Diverse Set of Broadly Applied Ligands

∗ Josiphos Ligands: From Discovery to Technical Applications

∗ Chiral Spiro Ligands

∗ Chiral Bisoxazoline Ligands

∗ PHOX Ligands

∗ Chiral Salen Complexes

∗ BINOL

∗ TADDOLate Ligands

∗ Cinchona Alkaloids

∗ Proline Derivatives
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Preface

BINAP

Introduction: Structural Consideration

Hydrogenation of Olefins

Hydrogenation of Ketones

Isomerization of Allylamines and Allylalcohols

Hydroboration, Hydrosilylation, Hydroacylation, and Hydroamination

Allylic Alkylation

Heck Reaction

Aldol and Mannich–Type Reactions

Nucleophilic Additions to Carbonyl and Imino Compounds

Alpha–Substitution Reactions of Carbonyl Compounds

Michael–Type Reactions

Conjugate Additions Using Organoboron and Grignard Reagents

Diels–Alder Reaction

Ene Reaction

Cyclization

Ring–Opening Reactions

Concluding Remarks

BISPHOSPHACYCLES –

FROM DuPHOS AND BPE TO A DIVERSE SET OF BROADLY APPLIED LIGANDS

Introduction

Development of Bisphosphacycle Ligands

Applications of Bisphosphacycle Ligands

Concluding Remarks

JOSIPHOS LIGANDS: FROM DISCOVERY TO TECHNICAL APPLICATIONS

Introduction and Background

Discovery and Development of the Josiphos Ligand Family

Why Are Josiphos Ligands So Effective?

Catalytic Profile of the Josiphos Ligand Family

Concluding Remarks

CHIRAL SPIRO LIGANDS

Introduction

Preparation of Chiral Spiro Ligands

Asymmetric Hydrogenation

Asymmetric Carbon–Carbon Bond Forming Reaction

Asymmetric Carbon–Heteroatom Bond Forming Reaction

Conclusion

CHIRAL BISOXAZOLINE LIGANDS

Introduction

Enantioselective Carbon–Carbon Bond Formation

Enantioselective Carbon–Heteroatom Bond Formation

Enantioselective Cycloaddition Reactions

Conclusions

PHOX LIGANDS

Introduction

Synthesis of PHOX Ligands

Nucleophilic Allylic Substitution

Decarboxylative Tsuji Allylations

Heck Reaction

Hydrogenation

Cycloadditions

Miscellaneous Reactions

Conclusion

CHIRAL SALEN COMPLEXES

Introduction

Synthesis of Chiral Salen Complexes

Structural Properties of Chiral Salen Complexes

Asymmetric Reactions Catalyzed by Chiral Salen Complexes

Conclusion and Outlook

BINOL

Introduction

Applications in Reduction and Oxidation

Metal/BINOL Chiral Lewis Acid Catalysts in Asymmetric C–C Bond Forming Reactions

Acid/Base Bifunctional Metal/BINOL Catalysts

BINOL in Organocatalysis

Summary

TADDOLATE LIGANDS

Introduction

Nucleophilic Additions to C=O Double Bonds

Nucleophilic Conjugate Additions to Electron–Deficient C=C Double Bonds

Nucleophilic Substitutions

Cycloaddition Reactions

Oxidation and Reduction Reactions

Miscellaneous Reactions

Conclusions

CINCHONA ALKALOIDS

Introduction

Metal Catalysis

Phase–Transfer Catalysis

Nucleophilic Catalysis

Base Catalysis

Cooperative and Multifunctional Catalysis

Conclusion

PROLINE DERIVATIVES

Introduction

Proline as Organocatalyst

Proline Analogs as Organocatalysts

5–Pyrrolidin–2–yltetrazole as Organocatalyst

Pyrrolidine–Based Sulfonamides as Organocatalysts

Pyrrolidine–Based Amides as Organocatalysts

Pyrrolidine Diamine Catalysts

Diarylprolinols or Diarylprolinol Ether Catalysts

Concluding Remarks

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Qi–Lin Zhou
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