Cycloaddition Reactions in Organic Synthesis 1st Edition by Shū Kobayashi, Karl Anker Jorgensen ISBN 9783527301591 3527301593

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ISBN 10:  3527301593

ISBN 13: 9783527301591

Author: Shū Kobayashi, Karl Anker Jorgensen

Cycloaddition reactions are among the most important tools for synthesis in organic chemistry, since these reactions are vital to the modern synthesis of natural products and biologically active substances.

Metal catalysis plays an increasingly important role in these reactions, often allowing several stereocenters to be selectively created and integrated in the target molecules. Kobayashi and Jorgensen’s handbook provides numerous examples of metal-catalyzed reactions, including [2+1], [3+2] and [4+2] cycloadditions. Important reactions such as carbo- and hetero-Diels-Alder, carbocyclic, cyclopropanation and 1,3-dipolar cycloaddition reactions are discussed. A large number of experimental procedures gives a concrete idea of the use of metal-catalyzed cycloaddition reactions in modern synthesis.

The book is aimed at chemists in industry or academia, who want to effectively use cycloadditions in their work.

Table of contents: 

1. Catalytic Asymmetric Diels-Alder Reactions – Yujiro Hayashi

1.1 Introduction

1.2 The Chiral Lewis Acid-catalyzed Diels-Alder Reaction

1.2.1 The Asymmetric Diels-Alder Reaction of α,β-Unsaturated Aldehydes as Dienophiles

Aluminum

Boron

Titanium

Iron

Ruthenium

Chromium

Copper

1.2.2 The Asymmetric Diels-Alder Reaction of α,β-Unsaturated Esters as Dienophiles

1.2.3 The Asymmetric Diels-Alder Reaction of 3-Alkenoyl-1,3-oxazolidin-2-ones as Dienophiles

Aluminum

Magnesium

Copper

Iron

Nickel

Titanium

Zirconium

Lanthanides

1.2.4 The Asymmetric Diels-Alder Reaction of Other Dienophiles

1.3 The Asymmetric Catalytic Diels-Alder Reaction Catalyzed by Base

1.4 Conclusions

1.5 Appendix
Acknowledgment
References

2. Recent Advances in Palladium-catalyzed Cycloadditions Involving Trimethylenemethane and its Analogs – Dominic M.T. Chan

2.1 General Introduction

2.2 Mechanism for [3+2] Carbocyclic Cycloaddition

2.3 Dynamic Behavior of TMM-Pd Complexes

2.4 Application in Organic Synthesis

General Comment

[3+2] Cycloaddition: The Parent TMM

Recent Applications in Natural and Unnatural Product Synthesis

Novel Substrates for TMM Cycloaddition

[3+2] Cycloaddition: Substituted TMM

Cyclopropyl-substituted TMM

Phenylthio-TMM

[3+2] Cycloaddition: Intramolecular Versions

Introduction and Substrate Synthesis

Synthesis of Bicyclo[3.3.0]octyl Systems

Synthesis of Bicyclo[4.3.0]nonyl Systems

Synthesis of Bicyclo[5.3.0]decyl Systems

Carboxylative Cycloadditions

Carbonyl Cycloadditions

Addition to Aldehydes

Addition to Ketones

Imine Cycloadditions

[4+3] Cycloadditions

[6+3] Cycloadditions

[3+3] Cycloaddition

2.5 Conclusions

References

3. Enantioselective [2+1] Cycloaddition: Cyclopropanation with Zinc Carbenoids – Scott E. Denmark and Gregory Beutner

3.1 Introduction

3.2 The Simmons-Smith Cyclopropanation – Historical Background

3.3 Structure and Dynamic Behavior of Zinc Carbenoids

Formation and Analysis of Zinc Carbenoids

Studies on the Schlenk Equilibrium for Zinc Carbenoids

3.4 Stereoselective Simmons-Smith Cyclopropanations

Substrate-directed Reactions

Auxiliary-directed Reactions

3.4.2.1 Chiral Ketals
3.4.2.2 Chiral Vinyl Ethers
3.4.3 In-situ Chiral Modification

Chirally Modified Reagents

Chirally Modified Substrates

3.4.4 Asymmetric Catalysis

General Considerations

Initial Discoveries

Defining the Role of Reaction Protocol

3.5 Simmons-Smith Cyclopropanations – Theoretical Investigations
3.6 Conclusions and Future Outlook
References

4. Catalytic Enantioselective Cycloaddition Reactions of Carbonyl Compounds – Karl Anker Jørgensen

4.1 Introduction

4.2 Activation of Carbonyl Compounds by Chiral Lewis Acids

The Basic Mechanisms of Cycloaddition Reactions of Carbonyl Compounds with Conjugated Dienes

4.3 Cycloaddition Reactions of Carbonyl Compounds

Reactions of Unactivated Aldehydes

Chiral Aluminum and Boron Complexes

Chiral Transition- and Lanthanide-metal Complexes

Reactions of Activated Aldehydes

Chiral Aluminum and Boron Complexes

Reactions of Ketones

Inverse Electron-demand Reactions

4.4 Summary
Acknowledgment
References

5. Catalytic Enantioselective Aza Diels-Alder Reactions – Shū Kobayashi

5.1 Introduction

5.2 Aza Diels-Alder Reactions of Azadienes

5.3 Aza Diels-Alder Reactions of Azadienophiles

5.4 A Switch of Enantiofacial Selectivity

5.5 Chiral Catalyst Optimization

5.6 Aza Diels-Alder Reactions of α-Imino Esters with Dienes

5.7 Aza Diels-Alder Reactions of 2-Azadienes

5.8 Perspective
References

6. Asymmetric Metal-catalyzed 1,3-Dipolar Cycloaddition Reactions – Kurt Vesterager Gothelf

6.1 Introduction

6.2 Basic Aspects of Metal-catalyzed 1,3-Dipolar Cycloaddition Reactions

The 1,3-Dipoles

Frontier Molecular Orbital Interactions

The Selectivities of 1,3-Dipolar Cycloaddition Reactions

6.3 Boron Catalysts for Reactions of Nitrones

6.4 Aluminum Catalysts for Reactions of Nitrones

6.5 Magnesium Catalysts for Reactions of Nitrones

6.6 Titanium Catalysts for Reactions of Nitrones and Diazoalkanes

6.7 Nickel Catalysts for Reactions of Nitrones

6.8 Copper Catalysts for Reactions of Nitrones

6.9 Zinc Catalysts for Reactions of Nitrones and Nitrile Oxides

6.10 Palladium Catalysts for Reactions of Nitrones

6.11 Lanthanide Catalysts for Reactions of Nitrones

6.12 Cobalt, Manganese, and Silver Catalysts for Reactions of Azomethine Ylides

6.13 Rhodium Catalysts for Reactions of Carbonyl Ylides

6.14 Conclusion
Acknowledgment
References

7. Aqua Complex Lewis Acid Catalysts for Asymmetric 3+2 Cycloaddition Reactions – Shuji Kanemasa

7.1 Introduction

7.2 DBFOX/Ph-Transition Metal Complexes and Diels-Alder Reactions

Preparation and Structure of the Catalysts

Diels-Alder Reactions

Structure of the Substrate Complexes

Tolerance of the Catalysts

Nonlinear Effect

7.3 Nitrone and Nitronate Cycloadditions

Role of MS 4A

Nickel(II) Complex-catalyzed Reactions

Reactions of Monodentate Dipolarophiles

Nitronate Cycloadditions

Diazo Cycloadditions

7.4 Screening of Lewis Acid Catalysts

Zinc Complex-catalyzed Asymmetric Reactions

Transition Structures

7.5 Conjugate Additions

7. Aqua Complex Lewis Acid Catalysts for Asymmetric 3+2 Cycloaddition Reactions – Shuji Kanemasa

7.5 Conjugate Additions

Thiol Conjugate Additions

Hydroxylamine Conjugate Additions

Michael Additions of Carbon Nucleophiles

7.6 Conclusion
References

8. Theoretical Calculations of Metal-catalyzed Cycloaddition Reactions – Karl Anker Jørgensen

8.1 Introduction

8.2 Carbo-Diels-Alder Reactions

Frontier-molecular-orbital Interactions for Carbo-Diels-Alder Reactions

Activation of the Dienophile by Lewis Acids, Interactions, Reaction Course, and Transition-state Structures

8.3 Hetero-Diels-Alder Reactions

Frontier-molecular-orbital Interactions for Hetero-Diels-Alder Reactions

Normal Electron-demand Hetero-Diels-Alder Reactions

Inverse Electron-demand Hetero-Diels-Alder Reactions

8.4 1,3-Dipolar Cycloaddition Reactions of Nitrones

Frontier-orbital Interactions for 1,3-Dipolar Cycloaddition Reactions of Nitrones

Normal Electron-demand Reactions

Inverse Electron-demand Reactions

8.5 Summary
Acknowledgment
References

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Tags: Shū Kobayashi, Karl Anker Jorgensen, Cycloaddition Reactions, Organic Synthesis