BOOK
Dienamine Catalysis for Organic Synthesis
Kengadarane Anebouselvy | Dhevalapally B Ramachary | Indresh Kumar
(2018)
Additional Information
Book Details
Abstract
In the past decade a new era in asymmetric catalysis has been realised by the discovery of L-proline induced chiral enamines from carbonyls. Inspired by this, researchers have developed many other primary catalytic species in situ, more recently secondary catalytic species such as aminals have been identified for use in asymmetric synthesis.
High-yielding asymmetric synthesis of bioactive and natural products through mild catalysis is an efficient approach in reaction engineering. In the early days, synthetic chemists mainly focused on the synthesis of complex molecules, with less attention on the reaction efficiency and eco-friendly conditions. Recent investigations have been directed towards the development of atom economy, eco-friendly and enantioselective synthesis for more targeted and efficient synthesis.
Building on the momentum of this rapidly expanding research area, Dienamine Catalysis for Organic Synthesis will provide a comprehensive introduction, from the preformed species, in situ generation and onto their applications in the synthesis of bioactive molecules and natural products.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Dienamine Catalysis for Organic Synthesis | i | ||
| Preface | vii | ||
| Dedication† | ix | ||
| Contents | xi | ||
| Chapter 1 - Introduction to Dienamine Chemistry | 1 | ||
| 1.1 Origin of Dienamine Catalysis | 1 | ||
| 1.2 Various Types of Dienamine Intermediates | 3 | ||
| 1.3 Significance of Dienamine Intermediates in Diels–Alder Type Reactions | 3 | ||
| 1.4 Conclusion | 7 | ||
| References | 7 | ||
| Chapter 2 - Synthesis and Applications of Preformed Dienamines | 10 | ||
| 2.1 Introduction | 10 | ||
| 2.2 1-Aminobuta-1,3-dienes | 11 | ||
| 2.3 2-Aminobuta-1,3-dienes | 16 | ||
| 2.4 Conclusion | 22 | ||
| References | 22 | ||
| Chapter 3 - Barbas Dienamines (2-Aminobuta-1,3-Dienes): Scope and Applications | 24 | ||
| 3.1 Introduction | 24 | ||
| 3.2 [4+2]-Cycloadditions | 25 | ||
| 3.3 Michael Reactions | 48 | ||
| 3.4 Conclusion | 50 | ||
| Acknowledgements | 51 | ||
| References | 51 | ||
| Chapter 4 - Ramachary’s Dienamines (Push–Pull Dienamines): In situ Generation and Applications | 53 | ||
| 4.1 Introduction | 53 | ||
| 4.2 Cascade or Domino Reactions | 54 | ||
| 4.3 [3+2]-Cycloadditions | 60 | ||
| 4.4 Baylis–Hillman-type Reactions | 62 | ||
| 4.5 Conclusion | 63 | ||
| Acknowledgement | 64 | ||
| References | 64 | ||
| Chapter 5 - Serebryakov–Jørgensen Dienamines (1-Aminobuta-1,3-Dienes): Different In situ Generation Methods and Applications in [4+2]-Cycloadditions | 65 | ||
| 5.1 Introduction | 65 | ||
| 5.2 Serebryakov–Jørgensen Dienamines Participating as Electron-rich Dienes | 66 | ||
| 5.3 Serebryakov–Jørgensen Dienamines Participating as Electron-rich Dienophiles | 81 | ||
| 5.4 Conclusion | 93 | ||
| References | 94 | ||
| Chapter 6 - Serebryakov–Jørgensen Dienamines (1-Aminobuta-1,3-Dienes): Different In situ Generation Methods and Applications in [2+2], [3+2] and a Few Other Cycloadditions | 96 | ||
| 6.1 Introduction | 96 | ||
| 6.2 Serebryakov–Jørgensen Dienamines in [2+2]-Cycloadditions | 97 | ||
| 6.3 Serebryakov–Jørgensen Dienamines in [3+2]-Cycloadditions | 102 | ||
| 6.4 Serebryakov–Jørgensen Dienamines in Other Cycloadditions | 107 | ||
| 6.4.1 [5+3]-Cycloadditions | 107 | ||
| 6.4.2 [5+2]-Cycloadditions | 107 | ||
| 6.4.3 [3+3]-Cycloadditions | 109 | ||
| 6.5 Conclusion | 110 | ||
| References | 111 | ||
| Chapter 7 - Asymmetric α-Selective and Remote γ-Selective Functionalization of Enals and Enones Through Serebryakov–Jørgensen Dienamines (1-Aminobuta-1,3-Dienes) | 112 | ||
| 7.1 Introduction | 112 | ||
| 7.2 Serebryakov–Jørgensen Dienamines in α-Selective Functionalization of Enals and Enones | 113 | ||
| 7.3 Serebryakov–Jørgensen Dienamines in the Remote Asymmetric γ-Selective Functionalization of Enals and Enones | 118 | ||
| 7.4 Conclusion | 133 | ||
| References | 134 | ||
| Chapter 8 - Applications of Serebryakov–Jørgensen Dienamines (1-Aminobuta-1,3-Dienes) in Domino or Cascade Reactions | 136 | ||
| 8.1 Introduction | 136 | ||
| 8.2 Serebryakov–Jørgensen Dienamines in Domino or Cascade Reactions | 137 | ||
| 8.3 Conclusion | 148 | ||
| References | 149 | ||
| Chapter 9 - Aminoenyne (2-Aminobuta-1,3-Enyne) Catalysis: In situ Generation and Synthetic Applications in Organic Reactions | 150 | ||
| 9.1 Introduction | 150 | ||
| 9.2 Aminoenyne Intermediates in Organic Reactions | 151 | ||
| 9.3 Conclusion | 156 | ||
| Acknowledgement | 157 | ||
| References | 157 | ||
| Chapter 10 - Trienamine-catalyzed Stereoselective Cycloadditions and Other Remote Functionalizations of Polyconjugated Enals/Enones | 158 | ||
| 10.1 Introduction | 158 | ||
| 10.2 Linear Trienamine Catalysis | 161 | ||
| 10.2.1 Trienamine Catalysis of Unsubstituted Dienals | 161 | ||
| 10.2.2 Trienamine Catalysis of Substituted Dienals | 163 | ||
| 10.2.3 Ortho-quinodimethanes and Related Trienamine Catalysis | 170 | ||
| 10.2.4 Remote Reactivity of Both Reacting Partners | 171 | ||
| 10.2.5 Trienamine Catalysis from Unconjugated Dienals | 174 | ||
| 10.2.6 Trienamine Catalysis with C=X as Dienophiles | 175 | ||
| 10.2.7 Hydrogen-bond Activation Directed Trienamine Catalysis | 177 | ||
| 10.3 Trienamine Catalysis Using Dienone | 181 | ||
| 10.3.1 Dienones Activation Through Trienamine Catalysis | 181 | ||
| 10.3.2 Catalysis Through Trienamine Derived from Unconjugated Enones | 182 | ||
| 10.4 Cross-conjugated Activation in Trienamine Catalysis | 185 | ||
| 10.5 Non-classical Trienamine Catalysis | 187 | ||
| 10.6 Conclusion | 189 | ||
| References | 190 | ||
| Chapter 11 - Tetraenamine-catalyzed Stereoselective Cycloadditions of Polyunsaturated Carbonyl Compounds | 194 | ||
| 11.1 Introduction | 194 | ||
| 11.2 [4+2]-Cycloadditions via Tetraenamine Intermediates | 196 | ||
| 11.3 Conclusions | 198 | ||
| References | 198 | ||
| Subject Index | 199 |