Synthetic and Stereochemical Aspects
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Table of contents
- Cover
- Contentsvii
- List of Contributorsxi
- Prefacexiii
- Chapter 1. Asymmetric Sulfoxidation–Chemical and Enzymatic1
- 1.1 Introduction2
- 1.2 Oxidation of sulfides bearing a removable chiral auxiliary3
- 1.3 Stoichiometric enantioselective oxidation of sulfides8
- 1.4 Catalytic chemical asymmetric sulfoxidation18
- 1.5 Biosulfoxidations27
- 1.6 Kinetic resolution30
- 1.7 Conclusion34
- References34
- Chapter 2. The Synthesis of Chiral Sulfoxides through Nucleophilic Displacement at Sulfur41
- 2.1 Introduction41
- 2.2 The Andersen procedure for the synthesis of enantiomerically enriched, chiral sulfoxides41
- 2.3 Adaptations of the Andersen procedure44
- 2.4 Application of chiral sulfinamides48
- 2.5 Application of chiral, cyclic sulfinamides52
- 2.6 Application of chiral, cyclic sulfites58
- References60
- Chapter 3. Conformational Preference of the Sulfinyl Group in Six-Membered Heterocycles63
- 3.1 Introduction64
- 3.2 Conformational equilibria of thiane-l-oxides65
- 3.3 Conformational analysis of oxathiane S-oxides76
- 3.4 Conformational analysis of dithiane S-oxides80
- 3.5. Conformational analysis of 5-sulfinyl-1,3-dioxanes86
- 3.6 Conformational analysis of 2-oxo-1,3,2-dioxathianes90
- References91
- Chapter 4. Applications of Chiral Sulfoxides as Stereocontrol Elements in Organic Synthesis97
- 4.1 Stereoselective reduction of β-ketosulfoxides: some applications in organic synthesis99
- 4.2 Stereocontrolled reactions of iminosulfoxides109
- 4.3 The stereocontrolled addition of nucleophiles to chiral vinylic sulfoxides121
- 4.4 Miscellaneous reaction types amenable to stereocontrol by acyclic chiral sulfoxides133
- 4.5 Cyclic sulfoxides in organic synthesis134
- 4.6 Application of chiral sulfoxides to the synthesis of natural products147
- 4.7 Concluding remarks151
- References151
- Chapter 5. The Chemistry of α,β - unsaturated Sulfoxides157
- 5.1 Introduction158
- 5.2 Preparation of optically active α,β -unsaturated sulfoxides158
- 5.3 Electrophilic additions to α,β -unsaturated sulfoxides164
- 5.4 Nucleophilic additions to α,β-unsaturated sulfoxides171
- 5.5 Pericyclic reactions of α,β -unsaturated sulfoxides191
- 5.6 Rearrangements Involving α,β -unsaturated sulfoxides215
- 5.7 Conclusion221
- References221
- Chapter 6. Preparation of Substituted 3-Sulfolenes and their use as Precursors for Diels–Alder Die229
- 6.1 Introduction229
- 6.2 Preparation of substituted 3-sulfolenes230
- 6.3 Substitution reactions of sulfolenes241
- 6.4 Formation of dienes from sulfolenes260
- 6.5 Applications of substituted sulfolenes in Diels–Alder-based syntheses272
- 6.6 Conclusion289
- References289
- Author Index293
- Subject Index303
The impact of organosulfur chemistry, especially in the areas of heterocyclic chemistry, stereocontrolled processes, and asymmetric synthesis, has led to a resurgence of interest in the field. This book is the secondin a series intended to provide coverage of topics of current interest throughout the whole range of organosulfur chemistry. Each volume is comprised of five or six chapters, each consisting of an in-depth, self-contained review in a well-defined area. This volume and its predecessor Organosulfur Chemistry, Synthetic Aspects will prove valuable references for researchers and practitioners in organic chemistry.
Key Features
* Methods of asymmetric sulfur oxidation processes
* Preparation of chiral sulfoxides in nucleophilic displacement at sulfur
* Conformational preferences of the sulfinyl group
* Preparation and chemistry of unsaturated sulfoxides
* Applications of sulfoxides as stereocontrol elements
* The chemistry of sulfolenes
Key Features
* Methods of asymmetric sulfur oxidation processes
* Preparation of chiral sulfoxides in nucleophilic displacement at sulfur
* Conformational preferences of the sulfinyl group
* Preparation and chemistry of unsaturated sulfoxides
* Applications of sulfoxides as stereocontrol elements
* The chemistry of sulfolenes