Asymmetric synthesis of three-membered rings / Hélène Pellissier, Alessandra Lattanzi and Renato Dalpozzo.

Format:

Book

Author/Creator:

Pellissier, Hélène, author.

Lattanzi, Alessandra, author.

Dalpozzo, Renato, author.

Language:

English

Subjects (All):

Organic compounds--Synthesis.

Organic compounds.

Asymmetric synthesis.

Chirality.

Physical Description:

1 online resource (591 pages) : illustrations

Edition:

1st ed.

Place of Publication:

Weinheim, Germany : Wiley-VCH, 2017.

Summary:

The first handbook to focus on the asymmetric synthesis of different types of three-membered rings. The outstanding and experienced authors have an excellent international reputation and cover cyclopropanes, epoxides and aziridines as well as chiral oxaziridines in equal measure. To this end, they describe in detail different synthetic approaches starting with chiral substrates as well as the application of chiral metal- or organocatalysts. Furthermore, methods for the kinetic resolution of initially racemic products are treated alongside recent advances and novel developments in established techniques for the synthesis of three-membered rings. With its structured composition this is of high interest to scientists in methodological and natural product synthesis as well as those in industrial and pharmaceutical chemistry.

Contents:

Cover

Title Page

Copyright

Contents

Preface

List of Abbreviations

Chapter 1 Asymmetric Cyclopropanation

1.1 Introduction

1.2 Simmons-Smith Cyclopropanation

1.2.1 Chiral Substrates

1.2.1.1 Chiral Allylic Alcohols

1.2.1.2 Chiral Allylic Amines

1.2.1.3 Chiral Acetal-Directed Cyclopropanations

1.2.1.4 Simple Chiral Alkenes

1.2.2 Chiral Auxiliaries

1.2.3 Chiral Catalysts

1.2.3.1 Charette's Ligand

1.2.3.2 Other Stoichiometric Ligands

1.2.3.3 Walsh' Procedure

1.2.3.4 True Catalytic Procedures

1.3 Transition-Metal-Catalyzed Decomposition of Diazoalkanes

1.3.1 Intermolecular Cyclopropanation

1.3.1.1 Chiral Auxiliaries

1.3.1.2 Chiral Catalysts: Cobalt

1.3.1.3 Chiral Catalysts: Copper

1.3.1.4 Chiral Catalysts: Rhodium

1.3.1.5 Chiral Catalysts: Ruthenium

1.3.1.6 Chiral Catalyst: Other Metals

1.3.2 Intramolecular Cyclopropanation

1.3.2.1 Chiral Auxiliaries and Chiral Compounds

1.3.2.2 Chiral Catalysts

1.3.3 Chiral Stoichiometric Carbenes

1.4 Michael-Initiated and Other Ring Closures

1.4.1 Chiral Substrates

1.4.2 Chiral Auxiliaries

1.4.2.1 Chiral Michael Acceptors

1.4.2.2 Chiral Nucleophiles

1.4.3 Organocatalysis

1.4.3.1 Ylides

1.4.3.2 Nitrocyclopropanation

1.4.3.3 Halocarbonyl Compounds

1.4.4 Metal Catalysis

1.4.5 Other Ring Closures

1.5 Miscellaneous Reactions

1.5.1 Rearrangement of Chiral Oxiranes

1.5.2 Cycloisomerization of 1,n-Enynes

1.5.3 Denitrogenation of Chiral Pyrazolines

1.5.4 C-H Insertion

1.5.5 Addition to Cyclopropenes

1.5.6 Other Methods

1.6 Conclusions

References

Chapter 2 Asymmetric Aziridination

2.1 Introduction

2.2 Aziridination Based on the Use of Chiral Substrates

2.2.1 Addition to Alkenes

2.2.1.1 Aziridination via Nitrene Transfer to Alkenes.

2.2.1.2 Aziridination via Addition-Elimination Processes

2.2.1.3 Miscellaneous Reactions

2.2.2 Addition to Imines

2.2.2.1 Methylidation of Imines

2.2.2.2 Aza-Darzens and Analogous Reactions

2.2.2.3 Addition/Elimination Processes

2.2.2.4 Miscellaneous Reactions

2.2.3 Addition to Azirines

2.2.4 Aziridination via Intramolecular Substitution

2.2.4.1 From 1,2-Amino Alcohols

2.2.4.2 From 1,2-Amino Halides

2.2.4.3 From 1,2-Azido Alcohols

2.2.4.4 From 1,2-Amino Sulfides and 1,2-Amino Selenides

2.2.4.5 From Epoxides

2.2.5 Miscellaneous Reactions

2.3 Aziridination Based on the Use of Chiral Catalysts

2.3.1 Aziridination via Nitrene Transfer to Alkenes

2.3.1.1 Cu-Catalyzed Aziridination

2.3.1.2 Rh-Catalyzed Aziridination

2.3.1.3 Ru-Catalyzed Aziridination

2.3.1.4 Catalysis by Other Metals

2.3.1.5 Organocatalyzed Aziridination

2.3.2 Aziridination via Carbene Transfer to Imines

2.3.2.1 Carbene Methodology

2.3.2.2 Sulfur-Ylide-Mediated Aziridination

2.3.3 Miscellaneous Reactions

2.3.4 Kinetic Resolutions of Aziridines

2.4 Conclusions

Chapter 3 Asymmetric Epoxidation

3.1 Introduction

3.2 Asymmetric Epoxidations Based on the Use of Chiral Auxiliaries

3.3 Asymmetric Metal-Catalyzed Epoxidations

3.3.1 Ti-, Zr-, Hf-Catalyzed Epoxidations

3.3.2 V-, Nb-, Ta-Catalyzed Epoxidations

3.3.3 Cr-, Mo-, W-Catalyzed Epoxidations

3.3.4 Mn-, Re-, Fe-, Ru-Catalyzed Epoxidations

3.3.5 Pt-, Zn-, Lanthanoid-Catalyzed Epoxidations

3.4 Asymmetric Organocatalyzed Epoxidations

3.4.1 Phase-Transfer Catalyst

3.4.2 Polyamino Acids and Aspartate-Derived Peracids

3.4.3 Chiral Dioxiranes, Iminium Salts, and Alkyl Hydroperoxides

3.4.4 Chiral Amines

3.5 Kinetic Resolution of Racemic Epoxides

3.6 Asymmetric Sulfur-Ylide-Mediated Epoxidations.

3.7 Asymmetric Darzens-Type Epoxidations

3.7.1 Chiral Auxiliary- and Reagent-Mediated Darzens Reactions

3.7.2 Catalytic Asymmetric Darzens Reactions

3.8 Other Ylide-Mediated Epoxidations

3.9 Asymmetric Biocatalyzed Synthesis of Epoxides

3.10 Conclusions

Chapter 4 Asymmetric Oxaziridination

4.1 Introduction

4.2 Oxaziridination Using Chiral Substrates

4.3 Oxaziridination Using Chiral Catalysts

4.4 Kinetic Resolutions

4.5 Conclusions

Chapter 5 Asymmetric Azirination and Thiirination

5.1 Introduction

5.2 Asymmetric Azirination

5.2.1 Neber Approaches

5.2.2 Elimination Approaches

5.2.3 Other Approaches

5.3 Asymmetric Thiirination

5.3.1 Conversion of Epoxides

5.3.2 Condensation of Sulfur‐Stabilized Carbanions to Carbonyl Compounds

5.3.3 Intramolecular Nucleophilic Substitution

5.3.4 Miscellaneous Reactions

5.4 Conclusions

Index

EULA.

Notes:

Includes bibliographical references at the end of each chapters and index.

Description based on online resource; title from PDF title page (ebrary, viewed April 19, 2017).

ISBN:

9783527802036

3527802037

9783527802012

3527802010

9783527802029

3527802029

OCLC:

982012804