Asymmetric Synthesis V2

Asymmetrie Synthesis, Volume 2: Stereodifferentiating Addition Reactions, Part A is concerned with asymmetric addition reactions.

This volume contains chapters that cover B-H additions across carbon-carbon and carbon-oxygen double bonds; carbonyl reductions using chiral modifications of lithium aluminum hydride and chiral dihydropyridines; additions of achiral and chiral nucleophiles to chiral and achiral aldehydes and ketones; organometal additions to chiral vinylic sulfoxides; and description of imine and enamine alkylations.

Chemists will find the book interesting.

Contenu

Contributors

Preface

1. Asymmetric Hydroboration

   I. Introduction

   II. Diisopinocampheylborane

   III. Dilongifolylborane

   IV. Limonylborane

   V. Monoisopinocampheylborane

   VI. Conclusion

   References

2. Reductions with Chiral Boron Reagents

   I. Introduction

   II. Chirally Modified Boranes

   III. Chirally Modified Borohydrides

   References

3. Reductions with Chiral Modifications of Lithium Aluminum Hydride

   I. Introduction

   II. Alcohol-Modified Lithium Aluminum Hydride

   III. Amine-Modified Lithium Aluminum Hydride

   IV. Amino Alcohol-Modified Lithium Aluminum Hydride

   V. Aminodiol-Modified Lithium Aluminum Hydride

   VI. Conclusions

   References

4. Reductions with Chiral Dihydropyridine Reagents

   I. Introduction

   II. Summary of the Mechanistic Studies of NADH Model Reactions

   III. Asymmetric Reductions with Chiral NADH Model Compounds

   IV. Factors Affecting Product Stereochemistry in Asymmetric Reductions with Chiral NADH Model Compounds

   V. Approach to Chiral NADH Models of Higher Stereoselectivity

   VI. Simulation of Enzyme Active Site Composed of Peptide Chain

   VII. Concluding Remarks

   References

5. Application of Cram's Rule: Addition of Achiral Nucleophiles to Chiral Substrates

   I. Introduction

   II. Variation of Reaction Conditions

   III. Application of Cram's Rule to Asymmetric Synthesis

   IV. Remote Stereochemical Control

   References

6. Addition of Chiral Nucleophiles to Aldehydes and Ketones

   I. Introduction

   II. Organometallic Reagents Used in a Chiral Environment

   III. Addition of Carbanions a to a Chiral Sulfoxide Group

   IV. Chiral Ester Enolates

   References

7. Noncatalytic Additions to a,ß-Unsaturated Carbonyl Compounds

   I. Introduction

   II. Conjugate Additions of Chiral a,ß-Unsaturated Carbonyl Derivatives

   III. Conjugate Additions with Chiral Nucleophiles

   References

8. Addition of Organometallic Reagents to Chiral Vinylic Sulfoxides

   I. Introduction

   II. 1-Alkenyl Sulfoxides

   III. 2-Alkenyl Sulfoxides

   IV. 2-Cycloalkenone Sulfoxides

   V. Conclusion

   References

9. Alkylation of Imine and Enamine Salts

   I. Introduction

   II. Formation of Azaallyl Metal Reagents and Enamines

   III. Structure of Azaallyl Metal Reagents

   IV. Electrophilic Substitution of Azaallyl Metal Regents and Enamines

   V. Asymmetric Syntheses Employing Chiral Azaallyl Metal Reagents

   VI. Asymmetric Syntheses Employing Chiral Enamines

   References

Index