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Dynamic Stereochemistry of Chiral Compounds ; Principles and Applications /
A comprehensive overview of fundamental concepts of asymmetric synthesis along with in-depth discussion.
| Clasificación: | Libro Electrónico |
|---|---|
| Autor principal: | |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
Cambridge :
Royal Society of Chemistry,
2007.
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| Temas: | |
| Acceso en línea: | Texto completo |
Tabla de Contenidos:
- CHAPTER 1: Introduction: CHAPTER 2: Principles of Chirality and Dynamic Stereochemistry-- 2.1. Stereochemistry of chiral compounds-- 2.2. Dynamic stereochemistry of cyclic and acyclic chiral compounds-- CHAPTER 3: Racemization, Enantiomerization and Diastereomerization-- 3.1. Classification of isomerization reactions of chiral compounds-- 3.1.1. Racemization-- 3.1.2. Enantiomerization-- 3.1.3. Diastereomerization-- 3.1.4. Epimerization and mutarotation-- 3.2. Stereomutations of chiral compounds: Mechanisms and energy barriers-- 3.2.1. Alkanes-- 3.2.2. Alkenes and annulenes-- 3.2.3. Allenes and cumulenes-- 3.2.4. Helicenes and phenanthrenes-- 3.2.5. Alkyl halides, nitriles and nitro compounds-- 3.2.6. Amines-- 3.2.7. Aldehydes, ketones and imines-- 3.2.8. Alcohols, ethers, acetals, and ketals-- 3.2.9. Carboxylic acids and derivatives-- 3.2.10. Amino acids-- 3.2.11. Silicon, phosphorus and sulfur compounds-- 3.2.12. Organometallic compounds-- 3.2.13. Supramolecular structures-- 3.3. Atropisomerization-- 3.3.1. Biaryls, triaryls and diarylacetylenes-- 3.3.2. Nonbiaryl atropisomers-- 3.3.3. Cyclophanes-- 3.3.4. Atropisomeric xenobiotics-- 3.4. Pharmacological and pharmacokinetic significance of racemization-- CHAPTER 4: Analytical Methods-- 4.1. Chiroptical methods-- 4.2. Variable-temperature NMR spectroscopy and proton/deuterium exchange measurements-- 4.3. Dynamic chromatography-- 4.3.1. Dynamic high performance liquid chromatography-- 4.3.2. Dynamic gas chromatography-- 4.3.3. Dynamic supercritical fluid chromatography and electrokinetic chromatography-- 4.4. Chromatographic and electrophoretic stopped-flow analysis-- 4.5. Comparison of analytical methods-- CHAPTER 5: Principles of Asymmetric Synthesis-- 5.1. Classification of asymmetric reactions-- 5.2. Kinetic and thermodynamic control-- 5.3. Asymmetric induction-- 5.3.1. Control of molecular orientation and conformation-- 5.3.2. Single and double stereodifferentiation-- CHAPTER 6: Asymmetric Synthesis with Stereodynamic Compounds: Introduction, Conversion and Transfer of Chirality-- 6.1. Asymmetric synthesis with chiral organolithium reagents-- 6.1.1.-Alkoxy- and -amino-substituted organolithium compounds-- 6.1.2. Sulfur-, phosphorus- and halogen-stabilized organolithium compounds-- 6.2. Atroposelective synthesis of axially chiral biaryls-- 6.2.1. Intramolecular atroposelective biaryl synthesis-- 6.2.2. Intermolecular atroposelective biaryl synthesis-- 6.2.3. Atroposelective ring construction-- 6.2.4. Desymmetrization of conformationally stable prochiral biaryls-- 6.2.5. Asymmetric transformation of stereodynamic biaryls-- 6.3. Nonbiaryl atropisomers-- 6.4. Chirality transfer and interconversion of chiral elements-- 6.4.1. Chirality transfer in SN2' and SE2' reactions-- 6.4.2. Rearrangements-- 6.4.2.1. 1,2-Chirality transfer-- 6.4.2.2. 1,3-Chirality transfer-- 6.4.2.3. 1,4-Chirality transfer-- 6.4.2.4. 1,5-Chirality transfer-- 6.4.3. Intermolecular chirality transfer-- 6.4.4. Transfer of stereogenicity between carbon and heteroatoms-- 6.4.5. Conversion of central chirality to other chiral elements-- 6.4.6. Conversion of axial chirality to other chiral elements-- 6.4.7. Conversion of planar chirality to other chiral elements-- 6.5. Self-regeneration of stereogenicity and chiral relays-- 6.5.1. Stereocontrolled substitution at a chiral center-- 6.5.2. Self-regeneration of stereocenters-- 6.5.3. Self-regeneration of chiral elements with stereolabile intermediates-- 6.5.4. Chiral relays-- 6.6. Asymmetric catalysis with stereolabile ligands-- 6.6.1. Stereodynamic achiral ligands-- 6.6.2. Stereolabile axially chiral ligands-- 6.7. Stereoselective synthesis in the solid state-- CHAPTER 7: Asymmetric Resolution and Transformation of Chiral Compounds under Thermodynamic and Kinetic Control-- 7.1. Scope and principles of asymmetric resolution and transformation-- 7.2. Asymmetric transformation of the first kind-- 7.3. Asymmetric transformation of the second kind-- 7.3.1. Crystallization-induced asymmetric transformation-- 7.3.2. Asymmetric transformation based on chromatographic separation-- 7.4. Kinetic resolution and dynamic kinetic resolution-- 7.4.1. Kinetic resolution-- 7.4.1.1. Enzyme-catalyzed kinetic resolution-- 7.4.1.2. Nonenzymatic kinetic resolution-- 7.4.1.3. Parallel kinetic resolution-- 7.4.2. Dynamic kinetic resolution-- 7.4.2.1. Enzyme-catalyzed dynamic kinetic resolution-- 7.4.2.2. Nonenzymatic dynamic kinetic resolution-- 7.5. Dynamic kinetic asymmetric transformation-- 7.6. Dynamic thermodynamic resolution-- CHAPTER 8: From Chiral Propellers to Unidirectional Motors-- 8.1. Stability and reactivity of stereodynamic gears-- 8.2. Structure and ring flipping of molecular propellers-- 8.3. Dynamic gearing in biaryl-, triaryl- and tetraaryl propellers-- 8.4. Molecular bevel gears-- 8.5. Vinyl propellers-- 8.6. Propeller-like coordination complexes with helicity control-- 8.7. Static gearing and cyclostereoisomerism-- 8.8. Molecular brakes, turnstiles and scissors-- 8.9. Chiral molecular switches-- 8.10. Stereodynamic sensors-- 8.11. Chiral molecular motors-- CHAPTER 9: Topological Isomerism and Chirality-- 9.1. Synthesis of catenanes and rotaxanes-- 9.1.1. Statistical methods-- 9.1.2. Template-assisted assembly-- 9.1.3. Topological isomerization-- 9.2. Chiral catenanes-- 9.3. Chiral rotaxanes-- 9.4. Knots and Borromean rings-- 9.5. Topological isomerism of shuttles, switches, sensors, and rotors-- GLOSSARY: Stereochemical Definitions and Terms.