Spiro Compounds - Synthesis and Applications

SPIRO COMPOUNDS
 
A comprehensive treatment of the latest research in, and applications of, spiro compounds
 
Spiro Compounds: Synthesis and Applications combines discussions of the latest advances in spiro compound research with the most cutting-edge, real-world applications of that knowledge. This book provides in-depth coverage of the history, significance, properties, synthetic methods, and applications of spiro compounds. As interest in spiro compounds grows due to their unique conformational features and their structural implications on biological systems, Spiro Compounds delivers fulsome treatments of advances in spiro compound synthesis (including stereoselective synthesis) methodologies.
 
With a special focus on the mechanisms of the reactions that lead to the synthesis of spiro compounds, chapters in the book cover topics such as:
* The history, significance, and unique properties of spiro compounds
* The most important methodologies for their synthesis
* The applications of spiro compounds in organic chemistry, biology, drug discovery
* The most important syntheses of natural products bearing a spiro ring
 
Perfect for academic and industrial chemists, this comprehensive discussion of spirocycles is an indispensable resource for those practicing in the field.

List of contents

List of Contributors xi
 
Preface xiii
 
1 Spiro Compounds: A Brief History 1
Marta Meazza
 
1.1 Notes on IUPAC Rules for Spiro Compounds 6
 
References 7
 
2 Selected Applications of Spirocycles in Medicinal Chemistry 9
Matthias Baud
 
2.1 Introduction 9
 
2.2 General Features 15
 
2.3 Property Optimization in Bioactive Compounds 17
 
2.4 Four-Membered Rings: Synthesis, Applications, and New Design
 
Principles 19
 
2.5 Further Examples 26
 
2.6 Conclusions 28
 
References 29
 
3 Recent Advances in the Asymmetric Synthesis of Spiro Compounds Through Cycloadditions 35
Alberto Vega-Peñaloza, Suva Paria, Luca Dell'Amico, and Xavier Companyó
 
3.1 Introduction 35
 
3.2 Organometallic Methodologies 36
 
3.2.1 Organometallic [3+2] Cycloaddition Strategies to Construct Spiro Compounds 36
 
3.2.2 Organometallic [4+2] Cycloaddition Strategies to Construct Spiro Compounds 42
 
3.2.3 Organometallic Miscellaneous Strategies to Construct Spiro
 
Compounds 44
 
3.3 Organocatalytic Methodologies 48
 
3.3.1 Organocatalytic [3+2] Cycloaddition Strategies to Construct Spiro Compounds 48
 
3.3.2 Organocatalytic [4+2] Cycloaddition Strategies to Construct Spiro Compounds 52
 
3.3.3 Organocatalytic [4+3] and [2+2] Cycloaddition and Switchable Strategies to Construct Spirocompounds 55
 
3.3.4 Organocatalytic Miscellaneous Strategies to Construct Spiro Compounds 60
 
References 62
 
4 Design and Synthesis of Spirocycles via Olefin Metathesis 65
Sambasivarao Kotha, Vikas R Aswar and Yellaiah Tangella
 
4.1 Introduction 65
 
4.2 Formation of Aza-spirocycles 84
 
4.3 Formation of Oxa-spirocycles 87
 
4.4 Miscellaneous Examples 97
 
References 98
 
5 Spirooxindoles: Synthesis via Organocatalytic Processes 103
Peng-Wei Xu, Xiao-Yuan Cui, Jin-Sheng Yu, and Jian Zhou
 
5.1 Introduction 103
 
5.2 Enamine and Iminium Catalysis 105
 
5.3 Chiral Nucleophilic Catalysis with Tertiary Phosphines or Amines 114
 
5.4 Chiral N-Heterocyclic Carbene Catalysis 120
 
5.5 Chiral Tertiary Amine-H-Bond Donor Bifunctional Catalysis 127
 
5.6 Chiral Hydrogen-Bonding Catalysis 142
 
5.7 Chiral Phosphoric Acid Catalysis 144
 
5.8 Chiral Phase-Transfer Catalysis 149
 
5.9 Chiral Organoiodine Catalysis 151
 
5.10 Conclusion 153
 
References 153
 
6 Spirooxindole Synthesis by Organometallic Processes 161
Albert Moyano
 
6.1 Introduction 161
 
6.2 Direct Construction of the Spirooxindole Unit by Cyclization Methodologies 161
 
6.2.1 Intramolecular Heck Reaction and Related Cyclizations 161
 
6.2.2 Alkylation-Cyclization of 3-Substituted Oxindoles 167
 
6.2.3 Cyclization of 3-Substituted Indoles 170
 
6.3 Two-component Annulation/Cycloaddition Methodologies 171
 
6.3.1 Cyclopropyl Spirooxindoles by [2+1] Cycloaddition Reactions 171
 
6.3.2 [2+2] Cycloaddition Reactions 173
 
6.3.3 [3+2] Annulation/Cycloaddition Reactions 175
 
6.3.4 [3+3] Cycloaddition Reactions 188
 
6.3.5 [4+1] Cycloaddition Reactions 189
 
6.3.6 [4+2] Cycloaddition/Annulation Reactions 190
 
6.3.7 [5+2] Cycloaddition Reactions 195
 
6.4 Miscellaneous Methods 195
 
6.4.1 Darzens Reaction of Isatins 195
 
6.4.2 Cyclization of 3,3-Disubstituted Oxindoles 198
 
6.4.3 Three-component Reactions 198
 
6.5 Conclusions 200
 
Acknowledgements 200
 
References 200
 
7 Enantioselective Synthes

About the author

Ramon Rios Torres, PhD is Associate Professor in Organic Chemistry at the University of Southampton. He is the author of more than 130 papers, 18 chapters in chemical books, and a patent. Dr. Rios has edited two books with Wiley: Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes and The Pauson-Khand Reaction: Scope, Variations and Applications.

Summary

A comprehensive treatment of the latest research in, and applications of, spiro compounds

Spiro Compounds: Synthesis and Applications combines discussions of the latest advances in spiro compound research with the most cutting-edge, real-world applications of that knowledge. This book provides in-depth coverage of the history, significance, properties, synthetic methods, and applications of spiro compounds. As interest in spiro compounds grows due to their unique conformational features and their structural implications on biological systems, Spiro Compounds delivers fulsome treatments of advances in spiro compound synthesis (including stereoselective synthesis) methodologies.

With a special focus on the mechanisms of the reactions that lead to the synthesis of spiro compounds, chapters in the book cover topics such as:
* The history, significance, and unique properties of spiro compounds
* The most important methodologies for their synthesis
* The applications of spiro compounds in organic chemistry, biology, drug discovery
* The most important syntheses of natural products bearing a spiro ring

Perfect for academic and industrial chemists, this comprehensive discussion of spirocycles is an indispensable resource for those practicing in the field.

Product details

• Authors: R Rios Torres, Ramon Rios Torres, Ramon (Universitat De Barcelona) Rios Torres
• Assisted by: Ramon Rios Torres (Editor), Rios Torres Ramon (Editor)
• Publisher: Wiley, John and Sons Ltd
• Languages: English
• Product format: Hardback
• Released: 30.09.2021
• EAN: 9781119567639
• ISBN: 978-1-119-56763-9
• No. of pages: 464
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; Chemie, Organische Chemie, ORGANIC CHEMISTRY, Katalyse, chemistry, Catalysis, Pharmaceutical & Medicinal Chemistry, Pharmazeutische u. Medizinische Chemie, Spiroverbindung