Principles of asymmetric synthesis:
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| Main Authors: | , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Amsterdam [u.a.]
Elsevier
2012
|
| Edition: | 2. ed. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XII, 555 S. graph. Darst. |
| ISBN: | 9780080448602 |
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Record in the Search Index
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|---|---|
| adam_text | Titel: Principles of asymmetric synthesis
Autor: Gawley, Robert E
Jahr: 2012
w
Foreword ix
Preface xi
1. Introduction, General Principles, and Glossary
of Stereochemical Terms 1
1.1. Why We Do Asymmetric Syntheses 1
1.2. What is an Asymmetric Synthesis? 2
1.3. Stereoselectivity, and What It Takes to Achieve It 4
1.4. Selectivity: Kinetic and Thermodynamic Control 7
1.5. Entropy, the Isoinversion Principle, and the Effect of Temperature
on Selectivity 10
1.6. Single and Double Asymmetric Induction 12
1.7. Kinetic Resolution 16
1.8. The Curtin—Hammett Principle 21
1.9. Asymmetric Transformations and Dynamic Resolutions 23
1.10. Asymmetric Catalysis and Nonlinear Effects 28
1.11. Glossary of Stereochemical Terms 34
References 58
2. Practical Aspects of Asymmetric Synthesis 63
2.1. Choosing a Method for Asymmetric Synthesis 63
2.2. How to Get Started 69
2.3. General Considerations for Analysis of Stereoisomers 71
2.4. Chromatography 73
2.4.1. A Chromatography Primer 73
2.4.2. Chiral Stationary Phase Chromatography 76
2.4.3. Achiral Derivatizing Agents 80
2.5. Nuclear Magnetic Resonance 80
2.5.1. Chiral Derivatizing Agents (CDAs) 81
2.5.2. Chiral Solvating Agents (CSAs) 85
2.6. Chiroptical Methods 86
2.7. Summary 91
References 92
3. Enolate, Azaenolate, and Organolithium Alkylations 97
3.1. Enolates and Azaenolates 97
3.1.1. Deprotonation of CarbonyIs 100
3.1.2. The Transition State for Enolate Alkylations 105
3.1.3. Enolate and Azaenolate Alkylations with Chiral Nucleophiles 110
3.1.4. Enolate and Azaenolate Alkylations with Chiral Electrophiles 139
vi
Contents
vii
3.2. Chiral Organolithiums 151
3.2.1. Inversion Dynamics of Chiral Organolithiums 153
3.2.2. Functionalized Organolithiums 157
3.2.3. Identifying the Stereochemically Defining Step 157
3.2.4. Asymmetrie Deprotonations 161
3.2.5. Unstabilized Organolithiums 165
References 168
4. 1,2- and 1,4-Additions to C=X Bonds 179
4.1. Cram s Rule: Open-Chain Model 180
4.1.1. The Karabatsos Model 180
4.1.2. Felkin s Experiments 181
4.1.3. The Bürgi—Dunitz Trajectory: A Digression 182
4.1.4. Back to the Cram s Rule Problem (Anh s Analysis) 186
4.1.5. Further Refinements 187
4.2. Cram s Rule: Rigid, Chelate, or Cyclic Model 191
4.3. Chiral Catalysts and Chiral Auxiliaries 196
4.3.1. Catalyzed Additions of Organometallic Compounds to Aldehydes 197
4.3.2. Addition of Organometallics to Azomethines 203
4.3.3. Additions of Organometallics to Pyridinium Ions 212
4.3.4. Hydrocyanations of Carbonyls 215
4.3.5. Hydrocyanations of Azomethines (the Strecker Reaction) 219
4.4. Conjugate Additions 221
4.4.1. Acyclic Esters and Ketones 222
4.4.2. Acyclic Amides and Imides 229
4.4.3. Cyclic Ketones and Lactones 232
References 237
5. Aldol and Michael Additions of Allyls, Enolates,
and Enolate Equivalents 245
5.1. 1,2-Allylations and Related Reactions 246
5.1.1. Simple Enantioselectivity 246
5.1.2. Simple Diastereoselectivity 248
5.1.3. Single Asymmetric Induction 249
5.1.4. Double Asymmetric Induction 251
5.1.5. Other Allyl Metals 254
5.2. Aldol Additions 258
5.2.1. Simple Diastereoselectivity 259
5.2.2. Single Asymmetric Induction 263
5.2.3. Organocatalysis of the Aldol Reaction and its Variants 285
5.2.4. Double Asymmetric Induction and Beyond: Synthetic
Applications of the Aldol Reaction 295
5.3. Michael Additions 301
5.3.1. Simple Diastereoselectivity: Basic Transition State Analysis 301
5.3.2. Chiral Donors 303
5.3.3. Chiral Michael Acceptors 315
vüi Contents
5.3.4. Interligand Asymmetrie Induction and Catalysis 316
5.3.5. Conjugate Addition of Nitrogen Nucleophiles 319
References 326
6. Cycloadditions and Rearrangements 335
6.1. Cycloadditions 335
6.1.1. The Diels—Alder Reaction 335
6.1.2. Hetero Diels—Alder Reaction 360
6.1.3. 1,3-Dipolar Cycloadditions 368
6.1.4. Summary 375
6.1.5. [2 + l]-Cyclopropanations and Related Processes 375
6.2. Rearrangements 395
6.2.1. [1,3]-Hydrogen Shifts 395
6.2.2. [2,3]-Wittig Rearrangements 401
6.2.3. Other Rearrangements 416
References 422
7. Reductions and Hydroborations 431
7.1. Reduction of Carbon—Heteroatom Double Bonds 431
7.1.1. Modified Lithium Aluminum Hydride 432
7.1.2. Modified Borane 434
7.1.3. Chiral Organoboranes 442
7.1.4. Chiral Transition Metal Catalysts 444
7.2. Reduction of Carbon—Carbon Bonds 463
7.3. Hydroborations 476
References 484
8. Oxidations 491
8.1. Epoxidations and Related Reactions 491
8.1.1. Early Approaches 491
8.1.2. Epoxidations 493
8.1.3. Sharpless Kinetic Resolution 504
8.1.4. Some Applications of Asymmetric Epoxidation and Kinetic
Resolution Procedures 506
8.1.5. Aziridinations 510
8.2. Asymmetric Dihydroxylation (AD) Reaction 510
8.2.1. Reaction Development 510
8.2.2. Applications of Enantioselective Dihydroxylations 518
8.3. a-Functionalization of Carbonyl Groups and Their Equivalents 521
8.3.1. Hydroxylations 522
8.3.2. Aminations and Halogenations 524
8.4. Miscellaneous Oxidations that Necessitate Differentiation
of Enantiotopic Groups 529
8.4.1. Oxidation of Sulfides 529
8.4.2. Group-Selective Oxidation of C—H Bonds 531
8.4.3. Group-Selective Oxidative Ring Expansions 531
References 539
Index
545
|
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| illustrated | Illustrated |
| indexdate | 2024-07-10T00:22:34Z |
| institution | BVB |
| isbn | 9780080448602 |
| language | English |
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| physical | XII, 555 S. graph. Darst. |
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| spelling | Gawley, Robert E. Verfasser aut Principles of asymmetric synthesis Robert E. Gawley and Jeffrey Aubé 2. ed. Amsterdam [u.a.] Elsevier 2012 XII, 555 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Aubé, Jeffrey Verfasser aut Erscheint auch als Online-Ausgabe Principles of asymmetric synthesis HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025219071&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Gawley, Robert E. Aubé, Jeffrey Principles of asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd |
| subject_GND | (DE-588)4135603-2 |
| title | Principles of asymmetric synthesis |
| title_auth | Principles of asymmetric synthesis |
| title_exact_search | Principles of asymmetric synthesis |
| title_full | Principles of asymmetric synthesis Robert E. Gawley and Jeffrey Aubé |
| title_fullStr | Principles of asymmetric synthesis Robert E. Gawley and Jeffrey Aubé |
| title_full_unstemmed | Principles of asymmetric synthesis Robert E. Gawley and Jeffrey Aubé |
| title_short | Principles of asymmetric synthesis |
| title_sort | principles of asymmetric synthesis |
| topic | Asymmetrische Synthese (DE-588)4135603-2 gnd |
| topic_facet | Asymmetrische Synthese |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025219071&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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