Proposed Mechanism and Stereochemical Outcomes of Metal-Catalyzed Reactions

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Table of contents

Acknowledgments
Abstract
List of Abbreviations
Chapter 1 Introduction：Methyl Coumalate
1.1 Introduction
1.2 Preparation of Methyl Coumalate
1.3 MC involved [4+2] Diels-Alder reaction
1.3.1 MC as dienes in Diels-Alder reactions
1.3.2. MC as Dienes to form Aromatics
1.3.3 MC as dienophile in Diels-Alder reactions
1.4. MC participates in [2+2] cycloadditions
1.5. MC reacts with 1,3 dipoles
1.6. Preparation of pyridin-2(1H)-one from MC
1.7. MC participates in [6+4] cycloaddition
1.8. MC via 1,6 Michael addition reactions
1.9. References
Chapter 2: β,γ -Unsaturated carboxylic acids by one-pot sequential double 1,6- addition of Grignard reagents onto methyl coumalate
2.1. Introduction
2.2. One-pot sequential double 1,6- addition of one same Grignard reagent
2.3. One-pot sequential double 1,6- addition of two different Grignard reagents
2.4 The studies on other substituted α-pyrone substrates
2.5. Proposed mechanism for stereoselective 1,6-double addition
2.6. Conclusions
2.7. Experimental Section
2.8. References
Chapter 3. Preparation of Substituted 2H-Pyrans via a Cascade Reaction from Methyl Coumalate and Activated Methylene Nucleophiles
3.1. Introduction of the project
3.2. Optimization of the reaction conditions for 2Hpyran synthesis
3.3. Substrate scope for preparation of 2H-pyran
3.4. Proposed unified mechanism
3.5. Conclusion
3.6. Experimental section
3.7. References
Chapter 4. A solvent-free, base-catalyzed domino reaction towards trifluoro methylated benzenes from bio-based methyl coumalate
4.1. Introduction
4.1.1. Cycloaddition towards trifluoromethylated benzenes
4.1.2. The synthesis of aromatics via a 6π-electrocyclic ring closure process
4.1.3. Our hypothesis from MC to CF3 benzene
4.2. Optimization of the Reaction Conditions
4.3. Application to a variety of trifluoromethyl benzenes
4.3.1 Gram scale synthesis of F-2b
4.4. Plausible mechanism for the cascade reaction leading to trifluoromethyl benzenes
4.6. Experimental section
4.7. Notes and references
Chapter 5. Bio-based methyl coumalate involved Morita-Baylis-Hillman reaction
5.1. General introduction of Morita-Baylis-Hillman reaction
5.2. Methyl coumalate involved MBH reaction
5.2.1.Optimization of reaction condition
5.2.2. Synthesis of bio-based MBH adducts
5.2.3. Plausible mechanism for the novel MBH reaction
5.2.4. Synthesis of diphenylmethanol derivative from MBH adduct
5.3. The regioselective transformation of MBH adducts
5.3.1 General introduction
5.3.2. The study of regioselective substitution
5.3.3. The study of enantioselective synthesis of bicyclic products
5.3.4. The transformation to hydroisobenzofuran and hydroisoindole cores
5.4 Asymmetric Morita-Baylis-Hillman reaction with MC
5.4.1 Bibliographic introduction
5.4.2. MC involved Asymmetric Morita-Baylis-Hillman reaction
5.5. Conclusion
5.6. Experimental section
5.7. References
Chapter 6. A solvent-free, catalyst-free Michael addition dearomatization strategy: A sustainable protocol towards novel fluorescent dyes
6.1. General introduction
6.2. Self promoted Michael addition dearomatization protocol
6.3. Plausible mechanism for the dearomatization
6.4. Photophysical properties of D-2j and its application for protein labelling
6.5. Conclusion
6.6. Experimental part
6.7 References
Conclusion