Dynamic stereochemistry of chiral compounds: principles and applications
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Cambridge
RSC Publ.
2008
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XIX, 512 S. graph. Darst. |
| ISBN: | 9780854042463 |
Staff View
MARC
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| adam_text | Contents
Chapter 1 Introduction 1
References 4
Chapter 2 Principles of Chirality and Dynamic Stereochemistry 6
2.1 Stereochemistry of Chiral Compounds 6
2.2 Dynamic Stereochemistry of Cyclic and Acyclic Chiral Compounds 15
References 27
Chapter 3 Racemization, Enantiomerization and Diastereomerization 29
3.1 Classification of Isomerization Reactions of Chiral Compounds 30
3.1.1 Racemization 31
3.1.2 Enantiomerization 34
3.1.3 Diastereomerization 36
3.1.4 Epimerization and Mutarotation 40
3.2 Stereomutations of Chiral Compounds: Mechanisms and Energy Barriers 44
3.2.1 Alkanes 44
3.2.2 Alkenes and Annulenes 46
3.2.3 Allenes and Cumulenes 52
3.2.4 Helicenes and Phenanthrenes 53
3.2.5 Alkyl Halides. Nitriles and Nitro Compounds 54
3.2.6 Amines 56
3.2.7 Aldehydes, Ketones and Imines 58
3.2.8 Alcohols, Ethers, Acetals, and Ketals 60
3.2.9 Carboxylic Acids and Derivatives 65
3.2.10 Amino Acids 68
3.2.11 Silicon, Phosphorus and Sulfur Compounds 71
3.2.12 Organometallic Compounds 74
3.2.13 Supramolecular Structures 80
v Contents
A
3.3 Atropisomerization °4
3.3.1 Biaryls, Triaryls and Diarylacetylenes 85
3.3.2 Nonbiaryl Atropisomers 94
3.3.3 Cyclophanes 104
3.3.4 Atropisomeric Xenobiotics 107
3.4 Pharmacological and Pharmacokinetic Significance of Racemization 109
References 1 2
Chapter 4 Analytical Methods 136
4.1 Chiroptical Methods 140
4.2 NMR Spectroscopy 143
4.3 Dynamic Chromatography 153
4.3.1 Dynamic High Performance Liquid Chromatography 159
4.3.2 Dynamic Gas Chromatography 164
4.3.3 Dynamic Supercritical Fluid Chromatography and Electrokinetic
Chromatography 167
4.4 Chromatographie and Electrophoretic Stopped-flow Analysis 168
4.5 Comparison of Analytical Methods 172
References 172
Chapter 5 Principles of Asymmetrie Synthesis 180
5.1 Classification of Asymmetrie Reactions 180
5.2 Kinetic and Thermodynamic Control 183
5.3 Asymmetrie Induction 186
5.3.1 Control of Molecular Orientation and Conformation 189
5.3.2 Single and Double Stereodifferentiation 194
References 198
Chapter 6 Asymmetrie Synthesis with Stereodynamic Compounds: Introduction, Conversion
and Transfer of Chirality 204
6.1 Asymmetrie Synthesis with Chiral Organolithium Reagents 205
6.1.1 a-Alkoxy- and oc-Amino-substituted Organolithium
Compounds 207
6.1.2 Sulfur-, Phosphorus- and Halogen-stabilized Organolithium
Compounds 212
6.2 Atroposelective Synthesis of Axially Chiral Biaryls 215
6.2.1 Intramolecular Atroposelective Biaryl Synthesis 217
6.2.2 Intermolecular Atroposelective Biaryl Synthesis 220
6.2.3 Atroposelective Ring Construction 224
6.2.4 Desymmetrization of Conformationally Stable Prochiral
Biaryls 225
6.2.5 Asymmetrie Transformation of Stereodynamic Biaryls 226
6.3 Nonbiaryl Atropisomers 231
6.4 Chirality Transfer and Interconversion of Chiral Elements 233
Contents xi
6.4.1 Chirality Transfer in SN2 and SE2 Reactions 234
6.4.2 Rearrangements 240
6.4.2.1 1,2-Chirality Transfer 241
6.4.2.2 1,3-Chirality Transfer 242
6.4.2.3 1,4-Chirality Transfer 250
6.4.2.4 1,5-Chirality Transfer 252
6.4.3 Intermolecular Chirality Transfer 254
6.4.4 Transfer of Stereogenicity Between Carbon and Heteroatoms 255
6.4.5 Conversion of Central Chirality to Other Chiral Elements 257
6.4.6 Conversion of Axial Chirality to Other Chiral Elements 261
6.4.7 Conversion of Planar Chirality to Other Chiral Elements 270
6.5 Self-regeneration of Stereogenicity and Chiral Relays 271
6.5.1 Stereocontrolled Substitution at a Chiral Center 271
6.5.2 Self-regeneration of Stereocenters 276
6.5.3 Self-regeneration of Chiral Elements with Stereolabile Intermediates 282
6.5.4 Chiral Relays 289
6.6 Asymmetrie Catalysis with Stereolabile Ligands 292
6.6.1 Stereodynamic Achiral Ligands 294
6.6.2 Stereolabile Axially Chiral Ligands 296
6.7 Stereoselective Synthesis in the Solid State 302
References 304
Chapter 7 Asymmetrie Resolution and Transformation of Chiral Compounds under
Thermodynamic and Kinetic Control 331
7.1 Scope and Principles of Asymmetrie Resolution and Transformation 334
7.2 Asymmetrie Transformation of the First Kind 334
7.3 Asymmetrie Transformation of the Second Kind 337
7.3.1 Crystallization-induced Asymmetrie Transformation 337
7.3.2 Asymmetrie Transformation based on Chromatographie
Separation 344
7.4 Kinetic Resolution and Dynamic Kinetic Resolution 346
7.4.1 Kinetic Resolution 346
7.4.1.1 Enzyme-catalyzed Kinetic Resolution 347
7.4.1.2 Nonenzymatic Kinetic Resolution 351
7.4.1.3 Parallel Kinetic Resolution 355
7.4.2 Dynamic Kinetic Resolution 359
7.4.2.1 Enzyme-catalyzed Dynamic Kinetic Resolution 360
7.4.2.2 Nonenzymatic Dynamic Kinetic Resolution 365
7.5 Dynamic Kinetic Asymmetrie Transformation 372
7.6 Dynamic Thermodynamic Resolution 378
References 382
Chapter 8 From Chiral Propellers to Unidirectional Motors 399
8.1 Stability and Reactivity of Stereodynamic Gears 399
8.2 Structure and Ring Flipping of Molecular Propellers 403
8.3 Dynamic Gearing in Biaryl-, Triaryl- and Tetraaryl Propellers 405
xjj Contents
8.4 Molecular Bevel Gears 411
8.5 Vinyl Propellers 414
8.6 Propeller-like Coordination Complexes with Helicity Control 418
8.7 Static Gearing and Cyclostereoisomerism 419
8.8 Molecular Brakes, Turnstiles and Scissors 421
8.9 Chiral Molecular Switches 423
8.10 Stereodynamic Sensors 432
8.11 Chiral Molecular Motors 435
References 437
Chapter 9 Topological Isomerism and Chirality 444
9.1 Synthesis of Catenanes and Rotaxanes 445
9.1.1 Statistical Methods 445
9.1.2 Template-assisted Assembly 447
9.1.3 Topological Isomerization 450
9.2 Chiral Catenanes 451
9.3 Chiral Rotaxanes 458
9.4 Knots and Borromean Rings 465
9.5 Topological Isomerism of Shuttles, Switches, Sensors, and Rotors 467
References 473
Glossary Stereochemical Definitions and Terms 480
Subject Index 503
|
| adam_txt |
Contents
Chapter 1 Introduction 1
References 4
Chapter 2 Principles of Chirality and Dynamic Stereochemistry 6
2.1 Stereochemistry of Chiral Compounds 6
2.2 Dynamic Stereochemistry of Cyclic and Acyclic Chiral Compounds 15
References 27
Chapter 3 Racemization, Enantiomerization and Diastereomerization 29
3.1 Classification of Isomerization Reactions of Chiral Compounds 30
3.1.1 Racemization 31
3.1.2 Enantiomerization 34
3.1.3 Diastereomerization 36
3.1.4 Epimerization and Mutarotation 40
3.2 Stereomutations of Chiral Compounds: Mechanisms and Energy Barriers 44
3.2.1 Alkanes 44
3.2.2 Alkenes and Annulenes 46
3.2.3 Allenes and Cumulenes 52
3.2.4 Helicenes and Phenanthrenes 53
3.2.5 Alkyl Halides. Nitriles and Nitro Compounds 54
3.2.6 Amines 56
3.2.7 Aldehydes, Ketones and Imines 58
3.2.8 Alcohols, Ethers, Acetals, and Ketals 60
3.2.9 Carboxylic Acids and Derivatives 65
3.2.10 Amino Acids 68
3.2.11 Silicon, Phosphorus and Sulfur Compounds 71
3.2.12 Organometallic Compounds 74
3.2.13 Supramolecular Structures 80
v Contents
A
3.3 Atropisomerization °4
3.3.1 Biaryls, Triaryls and Diarylacetylenes 85
3.3.2 Nonbiaryl Atropisomers 94
3.3.3 Cyclophanes 104
3.3.4 Atropisomeric Xenobiotics 107
3.4 Pharmacological and Pharmacokinetic Significance of Racemization 109
References 1' 2
Chapter 4 Analytical Methods 136
4.1 Chiroptical Methods 140
4.2 NMR Spectroscopy 143
4.3 Dynamic Chromatography 153
4.3.1 Dynamic High Performance Liquid Chromatography 159
4.3.2 Dynamic Gas Chromatography 164
4.3.3 Dynamic Supercritical Fluid Chromatography and Electrokinetic
Chromatography 167
4.4 Chromatographie and Electrophoretic Stopped-flow Analysis 168
4.5 Comparison of Analytical Methods 172
References 172
Chapter 5 Principles of Asymmetrie Synthesis 180
5.1 Classification of Asymmetrie Reactions 180
5.2 Kinetic and Thermodynamic Control 183
5.3 Asymmetrie Induction 186
5.3.1 Control of Molecular Orientation and Conformation 189
5.3.2 Single and Double Stereodifferentiation 194
References 198
Chapter 6 Asymmetrie Synthesis with Stereodynamic Compounds: Introduction, Conversion
and Transfer of Chirality 204
6.1 Asymmetrie Synthesis with Chiral Organolithium Reagents 205
6.1.1 a-Alkoxy- and oc-Amino-substituted Organolithium
Compounds 207
6.1.2 Sulfur-, Phosphorus- and Halogen-stabilized Organolithium
Compounds 212
6.2 Atroposelective Synthesis of Axially Chiral Biaryls 215
6.2.1 Intramolecular Atroposelective Biaryl Synthesis 217
6.2.2 Intermolecular Atroposelective Biaryl Synthesis 220
6.2.3 Atroposelective Ring Construction 224
6.2.4 Desymmetrization of Conformationally Stable Prochiral
Biaryls 225
6.2.5 Asymmetrie Transformation of Stereodynamic Biaryls 226
6.3 Nonbiaryl Atropisomers 231
6.4 Chirality Transfer and Interconversion of Chiral Elements 233
Contents xi
6.4.1 Chirality Transfer in SN2'and SE2'Reactions 234
6.4.2 Rearrangements 240
6.4.2.1 1,2-Chirality Transfer 241
6.4.2.2 1,3-Chirality Transfer 242
6.4.2.3 1,4-Chirality Transfer 250
6.4.2.4 1,5-Chirality Transfer 252
6.4.3 Intermolecular Chirality Transfer 254
6.4.4 Transfer of Stereogenicity Between Carbon and Heteroatoms 255
6.4.5 Conversion of Central Chirality to Other Chiral Elements 257
6.4.6 Conversion of Axial Chirality to Other Chiral Elements 261
6.4.7 Conversion of Planar Chirality to Other Chiral Elements 270
6.5 Self-regeneration of Stereogenicity and Chiral Relays 271
6.5.1 Stereocontrolled Substitution at a Chiral Center 271
6.5.2 Self-regeneration of Stereocenters 276
6.5.3 Self-regeneration of Chiral Elements with Stereolabile Intermediates 282
6.5.4 Chiral Relays 289
6.6 Asymmetrie Catalysis with Stereolabile Ligands 292
6.6.1 Stereodynamic Achiral Ligands 294
6.6.2 Stereolabile Axially Chiral Ligands 296
6.7 Stereoselective Synthesis in the Solid State 302
References 304
Chapter 7 Asymmetrie Resolution and Transformation of Chiral Compounds under
Thermodynamic and Kinetic Control 331
7.1 Scope and Principles of Asymmetrie Resolution and Transformation 334
7.2 Asymmetrie Transformation of the First Kind 334
7.3 Asymmetrie Transformation of the Second Kind 337
7.3.1 Crystallization-induced Asymmetrie Transformation 337
7.3.2 Asymmetrie Transformation based on Chromatographie
Separation 344
7.4 Kinetic Resolution and Dynamic Kinetic Resolution 346
7.4.1 Kinetic Resolution 346
7.4.1.1 Enzyme-catalyzed Kinetic Resolution 347
7.4.1.2 Nonenzymatic Kinetic Resolution 351
7.4.1.3 Parallel Kinetic Resolution 355
7.4.2 Dynamic Kinetic Resolution 359
7.4.2.1 Enzyme-catalyzed Dynamic Kinetic Resolution 360
7.4.2.2 Nonenzymatic Dynamic Kinetic Resolution 365
7.5 Dynamic Kinetic Asymmetrie Transformation 372
7.6 Dynamic Thermodynamic Resolution 378
References 382
Chapter 8 From Chiral Propellers to Unidirectional Motors 399
8.1 Stability and Reactivity of Stereodynamic Gears 399
8.2 Structure and Ring Flipping of Molecular Propellers 403
8.3 Dynamic Gearing in Biaryl-, Triaryl- and Tetraaryl Propellers 405
xjj Contents
8.4 Molecular Bevel Gears 411
8.5 Vinyl Propellers 414
8.6 Propeller-like Coordination Complexes with Helicity Control 418
8.7 Static Gearing and Cyclostereoisomerism 419
8.8 Molecular Brakes, Turnstiles and Scissors 421
8.9 Chiral Molecular Switches 423
8.10 Stereodynamic Sensors 432
8.11 Chiral Molecular Motors 435
References 437
Chapter 9 Topological Isomerism and Chirality 444
9.1 Synthesis of Catenanes and Rotaxanes 445
9.1.1 Statistical Methods 445
9.1.2 Template-assisted Assembly 447
9.1.3 Topological Isomerization 450
9.2 Chiral Catenanes 451
9.3 Chiral Rotaxanes 458
9.4 Knots and Borromean Rings 465
9.5 Topological Isomerism of Shuttles, Switches, Sensors, and Rotors 467
References 473
Glossary Stereochemical Definitions and Terms 480
Subject Index 503 |
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| id | DE-604.BV023161164 |
| illustrated | Illustrated |
| index_date | 2024-07-02T19:55:00Z |
| indexdate | 2024-07-09T21:11:44Z |
| institution | BVB |
| isbn | 9780854042463 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016332537 |
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| physical | XIX, 512 S. graph. Darst. |
| publishDate | 2008 |
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| publisher | RSC Publ. |
| record_format | marc |
| spelling | Wolf, Christian Verfasser aut Dynamic stereochemistry of chiral compounds principles and applications Christian Wolf Cambridge RSC Publ. 2008 XIX, 512 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Chiralité Stéréochimie Chirality Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Chirale Verbindungen (DE-588)4348527-3 gnd rswk-swf Organische Chemie (DE-588)4043793-0 gnd rswk-swf Stereochemie (DE-588)4129569-9 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 s Organische Chemie (DE-588)4043793-0 s DE-604 Chirale Verbindungen (DE-588)4348527-3 s Stereochemie (DE-588)4129569-9 s HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016332537&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Wolf, Christian Dynamic stereochemistry of chiral compounds principles and applications Chiralité Stéréochimie Chirality Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd Organische Chemie (DE-588)4043793-0 gnd Stereochemie (DE-588)4129569-9 gnd |
| subject_GND | (DE-588)4135603-2 (DE-588)4348527-3 (DE-588)4043793-0 (DE-588)4129569-9 |
| title | Dynamic stereochemistry of chiral compounds principles and applications |
| title_auth | Dynamic stereochemistry of chiral compounds principles and applications |
| title_exact_search | Dynamic stereochemistry of chiral compounds principles and applications |
| title_exact_search_txtP | Dynamic stereochemistry of chiral compounds principles and applications |
| title_full | Dynamic stereochemistry of chiral compounds principles and applications Christian Wolf |
| title_fullStr | Dynamic stereochemistry of chiral compounds principles and applications Christian Wolf |
| title_full_unstemmed | Dynamic stereochemistry of chiral compounds principles and applications Christian Wolf |
| title_short | Dynamic stereochemistry of chiral compounds |
| title_sort | dynamic stereochemistry of chiral compounds principles and applications |
| title_sub | principles and applications |
| topic | Chiralité Stéréochimie Chirality Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd Organische Chemie (DE-588)4043793-0 gnd Stereochemie (DE-588)4129569-9 gnd |
| topic_facet | Chiralité Stéréochimie Chirality Asymmetrische Synthese Chirale Verbindungen Organische Chemie Stereochemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016332537&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wolfchristian dynamicstereochemistryofchiralcompoundsprinciplesandapplications |