Stereoselective Multiple Bond Forming Transformations in Organic - Synthesi

Informationen zum Autor Jean Rodriguez is Professor and Director of the "Institut des Sciences Moléculaires de Marseille" at Aix-Marseille Université, with research interests including the development of new stereoselective domino and multicomponent reactions and their applications. He was awarded the ACROS prize in Organic Chemistry (1998) and the prize of the Division of Organic Chemistry (2009) from the French Chemical Society and was named a Distinguished Senior Member (2013) of the French Chemical Society. Damien Bonne is an assistant professor at Aix-Marseille Université, with research interests including the development of new asymmetric organocatalyzed methodologies and their application in stereoselective synthesis. Klappentext Combining the important research topic of multiple bond-forming transformations with green chemistry, this book helps chemists identify recent sustainable stereoselective synthetic sequences.* Combines the important research topic of multiple bond-forming transformations with green chemistry and sustainable development* Offers a valuable resource for preparing compounds with multiple stereogenic centers, an important field for synthetic chemists* Organizes chapters by molecular structure of final products, making for a handbook-style resource* Discusses applications of the synthesis of natural products and of drug intermediates* Brings together otherwise-scattered information about a number of key, efficient chemical reactions Zusammenfassung This book focuses on modern tools for efficient stereoselective synthesis proceeding exclusively with multiple bond-forming transformations (MBFTs), including examples of domino, multicomponent, or consecutive sequences. Inhaltsverzeichnis List of Contributors xiii Foreword xvii Preface xix 1 Definitions and Classifications of MBFTs 1 Damien Bonne and Jean Rodriguez 1.1 Introduction 1 1.2 Definitions 4 1.3 Conclusion and Outlook 6 References 7 PART I STEREOSELECTIVE SYNTHESIS OF HETEROCYCLES 9 2 Five-Membered Heterocycles 11 Hanmin Huang and Pan Xie 2.1 Introduction 11 2.2 Monocyclic Targets 12 2.2.1 1,3-Dipolar Cycloaddition 12 2.2.2 Michael Addition-Initiated Domino Process 20 2.2.3 Multicomponent Reactions 23 2.2.4 Carbohalogenation Reactions 26 2.2.5 Radical Processes 26 2.3 Fused Polycyclic Targets 28 2.3.1 Cycloaddition Reactions 28 2.3.2 Domino Cyclization Reactions 32 2.4 Bridged Polycyclic Targets 34 2.5 Conclusion and Outlook 36 References 37 3 Six-Membered Heterocycles 45 Giammarco Tenti, M. Teresa Ramos, and J. Carlos Menéndez 3.1 Introduction 45 3.2 Monocyclic Targets 47 3.2.1 Nitrogen-Only Heterocycles 47 3.2.2 Oxygen-Containing Heterocycles 58 3.3 Fused Polycyclic Targets 62 3.3.1 Nitrogen-Only Fused Polycyclic Targets 62 3.3.2 Oxygen-Containing Fused Polycyclic Targets 70 3.3.3 Sulfur-Containing Fused Polycyclic Targets 74 3.4 Bridged Polycyclic Targets 74 3.4.1 General Procedure for the Preparation of 2,6-DABCO-Derived Compounds 138 76 3.5 Polycyclic Spiro Targets 77 3.6 Summary and Outlook 79 References 79 4 Other Heterocycles 87 Qian Wang and Jieping Zhu 4.1 Introduction 87 4.2 Synthesis of Medium-Sized Monocyclic, Fused and Bridged Polycyclic Heterocycles 88 4.2.1 Ring Synthesis by Ring Transformation via Rearrangements/Ring Expansions 88 4.2.2 Ring Synthesis by Annulation 99 4.3 Summary and Outlook 109 References 109 PART II STEREOSELECTIVE SYNTHESIS OF CARBOCYCLES 115 5 Three- and Four-Membered Carbocycles 117 Renata Marcia de Figueiredo, Gilles Niel, and ...

List of contents

List of Contributors xiii
 
Foreword xvii
 
Preface xix
 
1 Definitions and Classifications of MBFTs 1
Damien Bonne and Jean Rodriguez
 
1.1 Introduction 1
 
1.2 Definitions 4
 
1.3 Conclusion and Outlook 6
 
References 7
 
PART I STEREOSELECTIVE SYNTHESIS OF HETEROCYCLES 9
 
2 Five-Membered Heterocycles 11
Hanmin Huang and Pan Xie
 
2.1 Introduction 11
 
2.2 Monocyclic Targets 12
 
2.2.1 1,3-Dipolar Cycloaddition 12
 
2.2.2 Michael Addition-Initiated Domino Process 20
 
2.2.3 Multicomponent Reactions 23
 
2.2.4 Carbohalogenation Reactions 26
 
2.2.5 Radical Processes 26
 
2.3 Fused Polycyclic Targets 28
 
2.3.1 Cycloaddition Reactions 28
 
2.3.2 Domino Cyclization Reactions 32
 
2.4 Bridged Polycyclic Targets 34
 
2.5 Conclusion and Outlook 36
 
References 37
 
3 Six-Membered Heterocycles 45
Giammarco Tenti, M. Teresa Ramos, and J. Carlos Menéndez
 
3.1 Introduction 45
 
3.2 Monocyclic Targets 47
 
3.2.1 Nitrogen-Only Heterocycles 47
 
3.2.2 Oxygen-Containing Heterocycles 58
 
3.3 Fused Polycyclic Targets 62
 
3.3.1 Nitrogen-Only Fused Polycyclic Targets 62
 
3.3.2 Oxygen-Containing Fused Polycyclic Targets 70
 
3.3.3 Sulfur-Containing Fused Polycyclic Targets 74
 
3.4 Bridged Polycyclic Targets 74
 
3.4.1 General Procedure for the Preparation of 2,6-DABCO-Derived Compounds 138 76
 
3.5 Polycyclic Spiro Targets 77
 
3.6 Summary and Outlook 79
 
References 79
 
4 Other Heterocycles 87
Qian Wang and Jieping Zhu
 
4.1 Introduction 87
 
4.2 Synthesis of Medium-Sized Monocyclic, Fused and Bridged Polycyclic Heterocycles 88
 
4.2.1 Ring Synthesis by Ring Transformation via Rearrangements/Ring Expansions 88
 
4.2.2 Ring Synthesis by Annulation 99
 
4.3 Summary and Outlook 109
 
References 109
 
PART II STEREOSELECTIVE SYNTHESIS OF CARBOCYCLES 115
 
5 Three- and Four-Membered Carbocycles 117
Renata Marcia de Figueiredo, Gilles Niel, and Jean-Marc Campagne
 
5.1 Introduction 117
 
5.2 Cyclopropane Derivatives 118
 
5.2.1 Organocatalysis and Related Reactions [Michael-Initiated Ring-Closure (MIRC) Reactions] 118
 
5.2.2 Organometallics and Metal Catalysis 123
 
5.2.3 Lewis Acid-Promoted Sequences 133
 
5.2.4 Pericyclic Domino Strategies 134
 
5.2.5 Radical Domino Strategies 135
 
5.3 Cyclobutane Derivatives 136
 
5.3.1 Organocatalyzed Cyclobutanations 136
 
5.3.2 Organometallics and Metal Catalysis 137
 
5.3.3 Acid- or Base-Promoted Transformations 143
 
5.3.4 Multicomponent Reactions (MCRs) 145
 
5.4 Summary and Outlook 146
 
References 146
 
6 Five-Membered Carbocycles 157
Vijay Nair and Rony Rajan Paul
 
6.1 Introduction 157
 
6.2 Monocyclic Targets 158
 
6.2.1 Metal-Catalyzed Reactions 158
 
6.2.2 Organocatalytic Reactions 158
 
6.2.3 Miscellaneous Reactions 167
 
6.3 Fused Polycyclic Targets 169
 
6.3.1 Metal-Catalyzed Reactions 169
 
6.3.2 Organocatalytic Reactions 170
 
6.3.3 Lewis Acid-Catalyzed Reactions 172
 
6.3.4 Miscellaneous Reactions 173
 
6.4 Bridged Polycyclic Targets 176
 
6.5 Conclusion and Outlook 178
 
References 179
 
7 Stereoselective Synthesis of Six-Membered Carbocycles 185
Muriel Amatore, Corinne Aubert, Marion Barbazanges, Marine Desage-El Murr, and Cyril Ollivier
 
7.1 Introduct

Product details

• Authors: Damien Bonne, Dieter Enders, J Rodriguez, Jean Rodriguez, Jean Bonne Rodriguez
• Assisted by: Bonne (Editor), Damien Bonne (Editor), Bonne Damien (Editor), Jean Rodriguez (Editor), Rodriguez Jean (Editor), Dieter Enders (Foreword), Enders Dieter (Foreword)
• Publisher: Wiley, John and Sons Ltd
• Languages: English
• Product format: Hardback
• Released: 22.04.2015
• EAN: 9781118672716
• ISBN: 978-1-118-67271-6
• No. of pages: 480
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; Chemie, Organische Chemie, ORGANIC CHEMISTRY, chemistry, Pharmaceutical & Medicinal Chemistry, Pharmazeutische u. Medizinische Chemie, Sustainable Chemistry & Green Chemistry, Nachhaltige u. Grüne Chemie