Asymmetric synthesis of nitrogen heterocycles:
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| Language: | English |
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Weinheim
Wiley-VCH
2009
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| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Item Description: | Literaturangaben |
| Physical Description: | XVI, 409 S. 24 cm |
| ISBN: | 9783527320363 |
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Titel: Asymmetric synthesis of nitrogen heterocycles
Autor: Royer, Jacques
Jahr: 2009
I"1
Contents
Prefece XIII
List of Contributors XV
Part One Asymmetrie Synthesis of Nitrogen Heterocycles Containing Only One
Heteroatom 1
1 Asymmetrie Synthesis of Three- and Four-Membered Ring
Heterocycles 3
Ciuliana Cardillo, Luca Centilucci and Alessandra Tolomelli
1.1 Substituted Aziridines 3
1.1.1 Generalities 3
1.1.2 Asymmetrie Aziridination via Cyclization Methods 6
1.1.2.1 Cyclization of a Nucleophilic N on an Electrophilic C (Pathway A) 7
1.1.2.2 Cyclization of a Stabilized Anion on an Electrophilic N (Pathway B) 9
1.1.3 Asymmetrie Aziridination via Cycloaddition Methods 12
1.1.3.1 Addition of Nitrenes to Alkenes 12
1.1.3.2 Reaction between Carbenes and Imines 16
1.1.4 Ring Transformation Methods 27
1.1.4.1 Aziridines from Epoxides 27
1.1.4.2 Aziridines from Other Heterocycles 30
1.1.5 Racemate Resolution 31
1.1.6 Asymmetrie Synthesis of Azirines 33
1.1.6.1 The Neber Reaction 33
1.1.6.2 Thermal or Photochemical Treatment of Vinyl Azides 34
1.1.6.3 Elimination from Aziridines 34
1.1.6.4 Resolution of Racemic Azirines 35
1.1.6.5 Oxidation of Aziridines 36
1.2 Substituted Monocyclic Azetidines and Carbocyclic-Fused Systems 36
1.2.1 Generalities 36
1.2.2 Cyclization Methods: Introduction 38
Asymmetrie Synthesis of Nitrogen Heterocycles. Edi ted by Jacques Royer
Copyright © 2009 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-32036-3
1.2.2.1 Cyclization methods: Enantiopure Azetidines via Formation of C-N
Bond 39
1.2.2.2 Cyclization Methods: Enantiopure Azetidines via Formation of C-C
Bond 40
1.2.3 Azetidines by Resolution of Racemates 42
1.2.4 Azetidines by Ring Transformation 44
References 45
2 Asymmetrie Synthesis of Five-Membered Ring Heterocycles 51
Pei-Qiang Huang
2.1 Monocyclic Pyrrolidines and Pyrrolidinones 51
2.1.1 Generalities 51
2.1.2 Cyclization Methods 52
2.1.2.1 Cyclization via C1/C5-N Bond Formation 52
2.1.2.2 Cyclization via C2-C3 Bond Formation 61
2.1.2.3 Cyclization Involving C3-C4 Bond Formation 62
2.1.3 Cycloaddition Methods 64
2.1.3.1 Cycloaddition Approach 64
2.1.3.2 Annulation Approach 66
2.1.4 Ring Transformation Methods 67
2.1.4.1 Ring Expansion Methods 67
2.1.4.2 Ring Contraction Methods 68
2.1.5 Substitution ofAlready Formed Heterocycle 68
2.1.5.1 By Nucleophilic Reaction of Pyrrolidinium Ions 71
2.1.5.2 By Nucleophilic Reaction ofCyclic Imides 72
2.1.5.3 By Nucleophilic Addition/Cycloaddition of Pyrrolidine Nitrones 74
2.1.5.4 By Functionalization of 2-Pyrrolines 76
2.1.5.5 By Enantioselective Reactions 77
2.1.5.6 By Functionalization at C3/C4 Positions of Pyrrolidines 77
2.2 Pyrrolines 79
2.2.1 Synthesis of Pyrrolines by Cyclization and Annulation Reactions 79
2.2.2 Synthesis of Pyrrolines by Substitution ofAlready Formed
Heterocycles 80
2.3 Fused Bicyclic Systems with Bridgehead Nitrogen 82
2.3.1 Pyrrolizidines 82
2.3.1.1 Through Extension of Methods for the Synthesis of Pyrrolidines 82
2.3.1.2 Other Methods for the Synthesis of Pyrrolizidines 83
2.3.1.3 Asymmetrie Synthesis of Polyhydroxylated Pyrrolizidines 85
2.4 Acknowledgments 87
References 87
3 Asymmetrie Synthesis of Six-Membered Ring Heterocycles 95
Naoki Toyooka
3.1 Introduction 95
3.2 Dihydropyridines 95
3.3 Tetrahydropyridines 98
3.3.1 Ring-Closing Metathesis (RCM) 98
3.3.2 Reduction of Pyridine Derivatives 101
3.3.3 Deracemization Processes 101
3.3.4 Michael Addition Followed by Elimination 102
3.3.5 Enamine Reaction 102
3.3.6 Electrocyclization 105
3.4 Monocyclic Piperidines and Carbocyclic Fused Systems 107
3.4.1 Generalities 107
3.4.2 Cyclization Methods 107
3.4.2.1 Nitrogen as a Nucleophile 108
3.4.2.2 C-C Bond Formation 113
3.4.3 Cycloaddition Methods 117
3.4.3.1 [4 + 2] Azadiene Cycloaddition 117
3.4.3.2 [4 + 2] Acylnitroso Cycloaddition 117
3.4.3.3 [3 + 2] Cycloaddition 119
3.4.4 Ring Transformation Methods J19
3.4.4.1 Ring Enlargement of Pyrrolidines to Substituted Piperidines 120
3.4.4.2 Ring Transformation ofLactones to 2-Piperidones 121
3.4.4.3 Ring Enlargement of y-Lactam to 2-Piperidones 122
3.4.5 Substitution of Already Formed Heterocycle 123
3.4.5.1 Phenylglycinol-Derived Oxazolidine 123
3.4.5.2 Asymmetrie Michael Addition 125
3.4.5.3 Nitrone Cycloaddition 127
3.4.5.4 Iminium Strategies 128
3.4.5.5 Oxidative Methods 131
3.5 Fused Tri- or Bicyclic System with Bridgehead Nitrogen 132
References 135
4 Asymmetrie Synthesis of Seven- and More-Membered Ring
Heterocydes 139
Yves Troin and Marie-Eve Sinibaldi
4.1 Substituted Azepines 139
4.1.1 Generalities 139
4.1.2 Cyclization Methods 142
4.1.2.1 Lactamization: C-N Bond Formation 142
4.1.2.2 Radical Cyclization 146
4.1.2.3 Intramolecular Cyclization 149
4.1.2.4 Oxidative Phenol Coupling Reaction 155
4.1.2.5 The Ring Closure Metathesis 155
4.1.3 Cycloaddition Methods 161
4.1.3.1 [5 + 2] Cycloaddition 162
4.1.3.2 [4 + 3] Cycloaddition 162
4.1.3.3 Nitrone Cycloaddition 162
4.1.3.4 Intramolecular Diels-Alder Reactions (IMDA) - [4 + 2]
Cycloaddition 163
4.1 A Ring Transformation Methods 163
4.1.4.1 Classical Methods 164
4.1.4.2 Ring Expansion 166
4.1.4.3 Substitution of Already Formed Heterocycles 169
4.2 Substituted Azocines 171
4.2.1 Azocines from Intramolecular Nucleophilic Substitution 172
4.2.2 Ring Transformations Methods 173
4.2.3 Cycloaddition Approaches to Azocines 174
4.2 A Ring-Closing Metathesis 175
4.3 Substituted Large Nitrogen-Containing Rings 177
References 181
Part Two Asymmetric Synthesis of Nitrogen Heterocycles with More Than One
Heteroatom 187
5 Asymmetric Synthesis of Three- and Four-Membered Ring Heterocycles
with More Than One Heteroatom 189
Steve Lanners and Gilles Hanquet
5.1 Introduction 189
5.2 Three-Membered N-Heterocycles with Two Heteroatoms 189
5.2.1 Diaziridines 190
5.2.1.1 Substrate-Controlled Diastereoselective Diaziridination Using Chiral
Enantiomerically Pure Amines 191
5.2.1.2 Substrate-Controlled Diastereoselective Diaziridination Using Chiral
Enantiomerically Pure Ketones 192
5.2.2 Diazirines 193
5.2.3 Oxaziridines 194
5.2.3.1 Chiral Peracidic Oxidation of Achiral Imines 195
5.2.3.2 Achiral Peracidic Oxidation of Chiral Nonracemic Imines 196
5.2.3.3 Photocyclization of Nitrones 207
5.3 Four-Membered N-Heterocycles with Two Heteroatoms 208
5.3.1 Diazetidines 208
5.3.2 Oxazetidines 210
5.3.2.1 Thiazetidines 212
5.4 Conclusions 217
References 217
6 Asymmetric Synthesis of Five-Membered Ring Heterocycles with More
Than One Heteroatom 223
Catherine Kadouri-Puchot and Claude Agami
6.1 Five-Membered Heterocycles with N and O Atoms 223
6.1.1 Oxazolidines 223
6.1.1.1 N-Alkyloxazolidines 224
6.1.1.2 N-Tosyl and N-Boc Oxazolidines 228
6.1.2 Oxazolines (4,5-dihydrooxazoles) 230
6.1.3 Oxazolidinones 235
6.1.3.1 Oxazolidin-2-ones 235
6.1.3.2 Oxazolidin-4-ones and 5-ones 242
6.1.4 Isoxazolines and Isoxazolidines 243
6.1.4.1 Isoxazolidines 244
6.1.4.2 Isoxazolines 246
6.2 Five-Membered Heterocycles with Two N Atoms 249
6.2.1 Imidazolidines and Imidazolidinones 249
6.2.1.1 Imidazolidines 249
6.2.1.2 Imidazolidinones 252
6.2.2 Pyrazolidines and Pyrazolines 255
6.2.2.1 Pyrazolidines 255
6.2.2.2 Pyrazolines 257
6.2.3 Pyrazolidinones 260
6.3 Five-Membered Heterocycles with N and S Atoms 263
6.3.1 Thiazolidines 263
6.3.1.1 I mino thiazolidines 267
6.3.1.2 Thiazolidinethiones 268
6.3.1.3 Thiazolidinones 269
6.3.2 Thiazolines 270
6.3.2.1 2-Thiazolines 270
6.3.2.2 3-Thiazolines 275
6.3.3 Sultams 276
References 281
7 Asymmetric Synthesis of Six-Membered Ring Nitrogen Heterocycles with
More Than One Heteroatom 293
Peter Matyus and P6I Tapolcsanyi
7.1 Six-Membered Rings with Another Heteroatom in the Same Ring 293
7.1.1 Pyridazines 293
7.1.1.1 Ring Closure of Optically Active Precursors 294
7.1.1.2 Diels-Alder Reactions 299
7.1.2 Pyrimidines 302
7.1.2.1 Formation of the Pyrimidine Ring 302
7.1.2.2 Stereoselective Transformation by the Involvement of the Pyrimidine
Ring 307
7.1.3 Piperazines 311
7.1.3.1 Formation of the Piperazine Ring 311
7.1.3.2 Stereoselective Transformation of the Piperazine Ring 327
7.1.4 Oxadiazines 332
7.1.4.1 1,2,5-Oxadiazines 332
7.1.4.2 1,3,4-Oxadiazines 332
7.1.5 Morpholines 335
7.1.5.1 Formation of the Morpholine Ring 335
7.1.5.2 Asymmetric Transformations with the Involvement of the Morpholine
Ring 352
References 359
8 Asymmetric Synthesis of Seven-Membered Rings with More Than One
Heteroatom 367
Jacques Royer
8.1 Diazepines 367
8.1.1 1,2-Diazepines 367
8.1.2 1,3-Diazepines 368
8.1.3 1,4-Diazepines 371
8.1.3.1 1,4-Benzodiazepines 371
8.1.3.2 Other 1,4-Diazepines 376
8.2 Oxazepines 378
8.2.1 1,2-Oxazepine 378
8.2.1.1 Diels-Alder Cycloaddition 378
8.2.1.2 Intramolecular 3 + 2 Cycloaddition 379
8.2.1.3 Pd-Catalyzed 4 + 3 Cycloaddition 3 79
8.2.1.4 Rearrangements 379
8.2.2 1,3-Oxazepines 380
8.2.2.1 N,O-Acetals 380
8.2.3 1,4-Oxazepines 383
8.2.3.1 Amino Alcohol Double Condensation 383
8.2.3.2 Other Cyclization Methods 383
8.2.3.3 Pd-Catalyzed Allene Cyclization 384
8.2.3.4 Radical Cyclization 385
8.2.3.5 Ring Enlargement 385
8.2.3.6 Cycloaddition 386
8.3 Thiazepines 386
8.3.1 1,2-Thiazepines 387
8.3.2 1,3-Thiazepines 387
8.3.3 1,4-Thiazepines 388
8.3.3.1 From Mercaptopropionic Acid Derivatives 388
8.3.3.2 From Amino Thiols 390
8.3.3.3 Others 391
References 392
Index 399 |
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| spelling | Asymmetric synthesis of nitrogen heterocycles ed. by Jacques Royer Weinheim Wiley-VCH 2009 XVI, 409 S. 24 cm txt rdacontent n rdamedia nc rdacarrier Literaturangaben Composés hétérocycliques - Synthèse Synthèse asymétrique Asymmetric synthesis Heterocyclic compounds Synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Stickstoffheterocyclen (DE-588)4183269-3 gnd rswk-swf Stickstoffheterocyclen (DE-588)4183269-3 s Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Royer, Jacques (DE-588)137759673 edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3159215&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017689772&sequence=000004&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Asymmetric synthesis of nitrogen heterocycles Composés hétérocycliques - Synthèse Synthèse asymétrique Asymmetric synthesis Heterocyclic compounds Synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd Stickstoffheterocyclen (DE-588)4183269-3 gnd |
| subject_GND | (DE-588)4135603-2 (DE-588)4183269-3 |
| title | Asymmetric synthesis of nitrogen heterocycles |
| title_auth | Asymmetric synthesis of nitrogen heterocycles |
| title_exact_search | Asymmetric synthesis of nitrogen heterocycles |
| title_full | Asymmetric synthesis of nitrogen heterocycles ed. by Jacques Royer |
| title_fullStr | Asymmetric synthesis of nitrogen heterocycles ed. by Jacques Royer |
| title_full_unstemmed | Asymmetric synthesis of nitrogen heterocycles ed. by Jacques Royer |
| title_short | Asymmetric synthesis of nitrogen heterocycles |
| title_sort | asymmetric synthesis of nitrogen heterocycles |
| topic | Composés hétérocycliques - Synthèse Synthèse asymétrique Asymmetric synthesis Heterocyclic compounds Synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd Stickstoffheterocyclen (DE-588)4183269-3 gnd |
| topic_facet | Composés hétérocycliques - Synthèse Synthèse asymétrique Asymmetric synthesis Heterocyclic compounds Synthesis Asymmetrische Synthese Stickstoffheterocyclen |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3159215&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017689772&sequence=000004&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT royerjacques asymmetricsynthesisofnitrogenheterocycles |