Stereoselective heterocycle synthesis via alkene difunctionalization : bulky phosphine ligands enable Pd-catalyzed arylhalogenation, arylcynation and diarylation /
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| Author / Creator: | Petrone, David A., author. |
|---|---|
| Imprint: | Cham, Switzerland : Springer, 2018. |
| Description: | 1 online resource |
| Language: | English |
| Series: | Springer theses : recognizing outstanding Ph. D. research Springer theses. |
| Subject: | |
| Format: | E-Resource Book |
| URL for this record: | http://pi.lib.uchicago.edu/1001/cat/bib/11654160 |
Table of Contents:
- Intro; Supervisor's Foreword; Preface; Parts of this thesis have been published in the following journal articles:; Acknowledgements; Contents; Abbreviations; List of Figures; List of Tables; List of Schemes; 1 Diastereoselective Synthesis of Heterocycles via Intramolecular Pd-Catalyzed Alkene Aryliodination; 1.1 Introduction; 1.1.1 Carbon-Carbon Bond Formation via Pd-Catalyzed Cross-coupling; 1.1.1.1 General Mechanisms for Cross-couplings and the Mizoroki-Heck Reaction; Oxidative Addition of Metal Complexes to Carbon-Halogen Bonds; Transmetallation.
- 1.1.3 Research Goals: Part 11.1.4 Results and Discussion: Chromans and Isochromans via a Diastereoselective Aryliodination; 1.1.4.1 Starting Material Preparation; 1.1.4.2 Optimization; 1.1.4.3 Examination of the Substrate Scope; 1.1.4.4 Limitations; 1.1.5 Research Goals: Part 2; 1.1.6 Development of the Diastereoselective Aryliodination of Chiral Amides: Application to the Chemical Synthesis of (+)-Corynoline; 1.1.6.1 Starting Material Preparation; 1.1.6.2 Optimization; 1.1.6.3 The Effect of Base on Diastereoselectivity; 1.1.6.4 Examination of the Substrate Scope; 1.1.6.5 Limitations.
- 1.1.6.6 Formal Synthesis of (+)-Corynoline1.1.7 Summary; 1.1.8 Experimental; References; 2 Pd-Catalyzed Diastereoselective Carbocyanation Reactions of Chiral N-Allyl Carboxamides and Indoles; 2.1 Introduction; 2.1.1 Palladium-Catalyzed Cyanation of Aromatic Halides; 2.1.2 Ni-Catalyzed Carbocyanation Proceeding via C-C Bond Cleavage; 2.1.3 Pd-Catalyzed Carbocyanation or Alkene and Alkynes; 2.1.3.1 Heck-Type Domino Reactions; 2.1.3.2 Other Classes of Pd-Catalyzed Carbocyanation; 2.1.4 Research Goals: Part 1.
- 2.1.5 Results and Discussion: Diastereoselective Pd-Catalyzed Arylcyanation of Chiral N-Allyl Carboxamides2.1.5.1 Starting Material Preparation; 2.1.5.2 Optimization; 2.1.5.3 Examination of the Substrate Scope; 2.1.5.4 Product Derivatization; 2.1.6 Research Goal: Part 2; 2.1.7 Results and Discussion: Diastereoselective Pd-Catalyzed Dearomative Arylcyanation of Indoles; 2.1.7.1 Starting Material Preparation; 2.1.7.2 Optimization; 2.1.7.3 Examination of the Substrate Scope; 2.1.7.4 Limitations; 2.1.7.5 Derivativation of Indoline Products; 2.1.8 Summary; 2.1.9 Experimental; References.