Domino reactions: concepts for efficient organic synthesis
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| Format: | Book |
| Language: | English |
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Weinheim
Wiley-VCH
2014
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XXIII, 621 S. Ill. 244 mm x 170 mm |
| ISBN: | 9783527334322 3527334327 |
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CONTENTS
PREFACE XIII
LIST OF CONTRIBUTORS XV
LIST OF ABBREVIATIONS XIX
INTRODUCTION 1
REFERENCES 4
1 TRANSITION-METAL-CATALYZED CARBONYLATIVE DOMINO REACTIONS 7
XIAO-FENG WU, HELJRIED NEUMANN, AND MATTHIAS BELTER
1.1 INTRODUCTION 7
1.2 TRANSITION-METAL-CATALYZED CARBONYLATIVE DOMINO REACTIONS 8
1.2.1 RUTHENIUM-CATALYZED CARBONYLATIVE DOMINO REACTIONS 8
1.2.2 RHODIUM-CATALYZED CARBONYLATIVE DOMINO REACTIONS 13
1.2.3 PALLADIUM-CATALYZED CARBONYLATIVE DOMINO REACTIONS 36
1.2.4 IRON-, COPPER-, NICKEL-, AND COBALT-CATALYZED CARBONYLATIVE DOMINO
REACTIONS 24
1.3 OUTLOOK 27
REFERENCES 27
2 METATHESIS REACTIONS IN DOMINO PROCESSES 31
KAMAL M. DAWOOD AND PETER METZ
2.1 DOMINO PROCESSES FEATURING SOLELY METATHESIS EVENTS 31
2.1.1 REACTIONS INVOLVING ONLY ALKENES 31
2.1.2 REACTIONS INVOLVING ALKENES AND ALKYNES 41
2.2 DOMINO PROCESSES FEATURING METATHESIS AND NON-METATHESIS
EVENTS 52
2.2.1 METATHESIS/REDOX TRANSFORMATION 52
2.2.2 METATHESIS/ISOMERIZATION 53
2.2.3 METATHESIS/CYCLOADDITION 56
2.2.4 METATHESIS/SUBSTITUTION 58
2.2.5 METATHESIS/CONJUGATE ADDITION 59
2.2.6 METATHESIS/CARBONYL OLEFINATION 62
HTTP://D-NB.INFO/103886089X
VI |
CONTENTS
2.3 CONCLUSION AND OUTLOOK 63
ACKNOWLEDGMENTS 63
REFERENCES 63
3 C-H ACTIVATION REACTIONS IN DOMINO PROCESSES 67
GAVIN CHIT TSUI AND MARK LAUTENS
3.1 HECK REACTIONS/C-H ACTIVATIONS 67
3.2 CARBOPALLADATIONS AND AMINOPALLADATIONS OF ALKYNES/C-H
ACTIVATIONS 72
3.3 PALLADIUM-CATALYZED/NORBORNENE-MEDIATED ORTHO C-H ACTIVATIONS 80
3.4 DOMINO REACTIONS INVOLVING HETEROATOM-DIRECTED C-H
ACTIVATIONS 96
3.5 CONCLUSIONS 101
REFERENCES 101
4 DOMINO REACTIONS INITIATED BY NUDEOPHILIC SUBSTITUTION 105
HIRIYAKKANAVAR ILA, ANAND ACHARYA, AND SARAVANAN PERUNCHERALATHAN
4.1 DOMINO SW/MICHAEL ADDITION AND RELATED REACTIONS 106
4.2 DOMINO REACTIONS INITIATED BY NUDEOPHILIC RING OPENING OF
AZIRIDINES, EPOXIDES, AND ACTIVATED CYDOPROPANES 115
4.3 DOMINO S^/BROOK REARRANGEMENTS 127
REFERENCES 138
5 RADICAL REACTIONS IN DOMINO PROCESSES 141
GUANGHUI AN AND GUIGEN LI
5.1 INTRODUCTION 141
5.2 RADICAL/CATION DOMINO PROCESSES 143
5.3 RADICAL/ANIONIC DOMINO PROCESSES 148
5.4 DOMINO RADICAL/RADICAL PROCESS 154
5.5 RADICAL/PERICYCLIC DOMINO PROCESSES 172
5.6 ASYMMETRIC RADICAL DOMINO PROCESSES 174
5.6.1 CHIRAL AUXILIARY-DIRECTED ASYMMETRIC RADICAL DOMINO PROCESSES 174
5.6.2 CHIRAL CATALYST-DRIVEN ASYMMETRIC RADICAL DOMINO PROCESSES 176
5.7 CONCLUSION AND OUTLOOK 178
ACKNOWLEDGMENTS 179
REFERENCES 179
6 PERICYCLIC REACTIONS IN DOMINO PROCESSES 183
LUKAS J. PATALAG
AND DANIEL B. WERZ
6.1 INTRODUCTION 183
6.2 CYDOADDITIONS 184
6.2.1 CYDOADDITION/CYDOADDITION 184
6.2.2 CYDOADDITION/CYDOREVERSION 185
6.2.3 CYDOADDITION/SIGMATROPIC REARRANGEMENT 188
6.2.4 CYCLOADDITION/ELECTROCYDIZATION 189
CONTENTS
I VII
6.2.5 CYCLOADDITION/MIXED TRANSFORMATIONS 191
6.3 SIGMATROPIC REARRANGEMENTS 192
6.3.1 SIGMATROPIC REARRANGEMENT/SIGMATROPIC REARRANGEMENT 192
6.3.2 SIGMATROPIC REARRANGEMENT/CYCLOADDITION 195
6.3.3 SIGMATROPIC REARRANGEMENT/ELECTROCYCLIZATION 196
6.3.4 SIGMATROPIC REARRANGEMENT/MIXED TRANSFORMATIONS 199
6.4 ELECTROCYCLIZATIONS 201
6.4.1 ELECTROCYDIZATION/ELECTROCYDIZATION 201
6.4.2 ELECTROCYCLIZATION/CYDOADDITION 202
6.4.3 ELECTROCYDIZATION/SIGMATROPIC REARRANGEMENT 205
6.4.4 ELECTROCYDIZATION/MIXED TRANSFORMATIONS 208
6.5 MIXED TRANSFORMATIONS 209
6.5.1 MIXED TRANSFORMATIONS FOLLOWED BY PERICYCLIC REACTIONS 209
6.5.2 CASCADES OF CARBOPALLADATIONS FOLLOWED BY PERICYCLIC REACTIONS 211
6.5.3 DOMINO KNOEVENAGEL/HETERO DIELS-ALDER REACTION 214
6.6 CONCLUDING REMARKS 214
ACKNOWLEDGMENTS 215
REFERENCES 215
7 MODERN DOMINO REACTIONS CONTAINING A MICHAEL ADDITION REACTION 219
SCOTT G. STEWART
7.1 INTRODUCTION 219
7.2 FORMATION OF ACYCLIC PRODUCTS 221
7.3 FORMATION OF CARBOCYDES 225
7.4 FORMATION OF O-HETEROCYDES 236
7.5 FORMATION OF N-HETEROCYCLES 250
7.6 FORMATION OF S-HETEROCYDES 257
7.7 FORMATION OF HETEROCYDES CONTAINING NITROGEN AND OXYGEN 260
REFERENCES 262
8 ALDOL REACTIONS IN DOMINO PROCESSES 267
CHRISTOPH SCHNEIDER AND MICHAEL BOOMHOFF
8.1 INTRODUCTION 267
8.2 DOMINO PROCESSES WITH THE ALDOL REACTION AS FIRST STEP 267
8.2.1 ALDOL-LACTONIZATION REACTIONS 267
8.2.2 ALDOL/PRINS REACTIONS 270
8.2.3 ALDOL/ACETALIZATION REACTIONS 272
8.2.4 ALDOL-TISHCHENKO REACTIONS 273
8.2.5 VINYLOGOUS ALDOL/MICHAEL REACTIONS 276
8.3 DOMINO PROCESSES WITH THE ALDOL REACTION AS SUBSEQUENT STEP 277
8.3.1 CONJUGATE ADDITION/ALDOL REACTIONS 277
8.3.1.1 ADDITION OF CARBON NUDEOPHILES 277
8.3.1.2 ADDITION OF SULFUR NUDEOPHILES 281
8.3.1.3 ADDITION OF OXYGEN AND NITROGEN NUDEOPHILES 283
8.3.1.4 IODO-ALDOL REACTIONS 285
VIIII
CONTENTS
8.3.1.5 REDUCTIVE ALDOL REACTIONS 287
8.3.2 ISOMERIZATION/ALDOL REACTIONS 289
8.3.3 WITTIG REARRANGEMENT/ALDOL REACTIONS 290
8.3.4 CYCLOADDITION/ALDOL REACTIONS 290
8.4 CONCLUSION AND OUTLOOK 292
REFERENCES 292
9 OXIDATIONS AND REDUCTIONS IN DOMINO PROCESSES 295
GOVINDASAMY SEKAR, LYYANAR KARTHILCEYAN, AND DHANDAPANI GANAPATHY
9.1 INTRODUCTION 295
9.2 DOMINO REACTIONS INITIATED BY OXIDATION OR REDUCTION REACTION 296
9.2.1 DOMINO REACTIONS INITIATED BY AN OXIDATION REACTION 296
9.2.2 DOMINO REACTIONS INITIATED BY REDUCTION REACTION 301
9.3 DOMINO REACTIONS HAVING OXIDATION IN MIDDLE OF THE SEQUENCE 312
9.4 DOMINO REACTIONS TERMINATED BY OXIDATION OR REDUCTION
REACTION 313
9.4.1 DOMINO REACTIONS TERMINATED BY OXIDATION REACTION 313
9.4.2 DOMINO REACTIONS TERMINATED BY REDUCTION REACTION 314
9.5 CONCLUSION 319
ACKNOWLEDGMENTS 319
REFERENCES 319
10 ORGANOCATALYSIS IN DOMINO PROCESSES 325
H&ENE
PELLISSIER
10.1 INTRODUCTION 325
10.2 ONE- AND TWO-COMPONENT DOMINO REACTIONS 326
10.2.1 DOMINO REACTIONS INITIATED BY THE MICHAEL REACTION 327
10.2.1.1 DOMINO MICHAEL/MICHAEL REACTIONS 327
10.2.1.2 DOMINO MICHAEL/ALDOL REACTIONS 334
10.2.1.3 DOMINO MICHAEL/INTRAMOLECULAR HETEROCYCLIZATION REACTIONS 340
10.2.1.4 DOMINO MICHAEL/INTRAMOLECULAR ALKYLATION REACTIONS 349
10.2.1.5 DOMINO MICHAEL/(AZA)-HENRY REACTIONS 352
10.2.1.6 DOMINO MICHAEL/KNOEVENAGEL REACTIONS 355
10.2.1.7 DOMINO MICHAEL/AZA-MORITA-BAYLIS-HILLMAN REACTIONS 357
10.2.1.8 DOMINO MICHAEL/MANNICH REACTIONS 357
10.2.1.9 OTHER DOMINO REACTIONS INITIATED BY THE MICHAEL REACTION 359
10.2.2 DOMINO REACTIONS INITIATED BY OTHER REACTIONS 361
10.2.2.1 DOMINO REACTIONS INITIATED BY THE INDIRECT MANNICH REACTION 361
10.2.2.2 DOMINO REACTIONS INITIATED BY THE (AZA)-MORITA-BAYLIS-HILLMAN
REACTION 363
10.2.2.3 DOMINO REACTIONS INITIATED BY THE FRIEDEL-CRAFTS REACTION 364
10.2.2.4 MISCELLANEOUS DOMINO REACTIONS 365
10.3 MULTICOMPONENT REACTIONS 371
10.3.1 MULTICOMPONENT REACTIONS INITIATED BY THE MICHAEL REACTION 371
10.3.1.1 MICHAEL REACTIONS OF A,P-UNSATURATED ALDEHYDES 371
CONTENTS
| IX
10.3.1.2 MICHAEL REACTIONS OF OTHER A.FI-UNSATURATED CARBONYL
COMPOUNDS 378
10.3.1.3 MICHAEL REACTIONS OF NITROOLEFINS 380
10.3.2 MULTICOMPONENT REACTIONS INITIATED BY THE KNOEVENAGEL REACTION
385
10.3.3 MULTICOMPONENT REACTIONS BASED ON THE MANNICH REACTION 388
10.3.4 MULTICOMPONENT REACTIONS BASED ON THE BIGINELLI REACTION 392
10.3.5 MULTICOMPONENT REACTIONS BASED ON THE HANTZSCH REACTION 394
10.3.6 MULTICOMPONENT REACTIONS BASED ON THE STRECKER REACTION 395
10.3.7 MULTICOMPONENT REACTIONS BASED ON THE PETASIS REACTION 397
10.3.8 1,3-DIPOLAR CYCLOADDITION-BASED MULTICOMPONENT REACTIONS 398
10.3.9 MISCELLANEOUS MULTICOMPONENT REACTIONS 400
10.4 CONCLUSIONS 405
REFERENCES 405
11 METAL-CATALYZED ENANTIO- AND DIASTEREOSELECTIVE C-C BOND-FORMING
REACTIONS IN DOMINO PROCESSES 419
SHINOBU TAKIZAWA AND HIROAKI SASAI
11.1 DOMINO REACTION INITIATED BY C-C BOND FORMATION 419
11.1.1 DOMINO REACTION INITIATED BY CONJUGATE ADDITION 419
11.1.2 DOMINO REACTION INITIATED BY CYCLOADDITION 433
11.1.3 DOMINO REACTION INITIATED BY CARBOMETALATION 435
11.2 DOMINO REACTION INITIATED BY C-H BOND FORMATION 435
11.2.1 DOMINO REACTION INITIATED BY CONJUGATE ADDITION 435
11.3 DOMINO REACTION INITIATED BY C-N BOND FORMATION 442
11.3.1 DOMINO REACTION INITIATED BY IMINE FORMATION 442
11.3.2 DOMINO REACTION BASED ON CYCLOADDITION 443
11.4 DOMINO REACTION INITIATED BY C-0 BOND FORMATION 445
11.4.1 DOMINO REACTION INITIATED BY CARBONYL YLIDE FORMATION 445
11.4.2 DOMINO REACTION INITIATED BY OXONIUM YLIDE FORMATION 450
11.4.3 DOMINO REACTION BASED ON CYCLOADDITION 452
11.4.4 DOMINO REACTION BASED ON PD(II)/PD(IV) CATALYSIS 454
11.4.5 DOMINO REACTION BASED ON A WACKER OXIDATION 454
11.5 DOMINO REACTION INITIATED BY C-B AND C-SI BOND FORMATION 455
11.5.1 DOMINO REACTION INITIATED BY CONJUGATE ADDITION 456
11.6 CONCLUSION AND OUTLOOK 457
REFERENCES 458
12 DOMINO PROCESSES UNDER MICROWAVE IRRADIATION, HIGH PRESSURE, AND IN
WATER 463
BO JIANG, SHU-JIANG
TU, AND GUIGEN LI
12.1 INTRODUCTION 463
12.2 MICROWAVE-ASSISTED DOMINO REACTIONS 464
12.2.1 INTRAMOLECULAR DOMINO REACTIONS UNDER MICROWAVE HEATING 464
12.2.2 TWO-COMPONENT DOMINO REACTION UNDER MICROWAVE HEATING 465
12.2.3 MULTICOMPONENT DOMINO REACTIONS UNDER MICROWAVE HEATING 472
X |
CONTENTS
12.3 AQUEOUS DOMINO REACTIONS 480
12.3.1 TWO-COMPONENT DOMINO REACTIONS IN WATER 480
12.3.2 MULTICOMPONENT DOMINO REACTION IN WATER 484
12.4 HIGH-PRESSURE-PROMOTED DOMINO REACTIONS 489
12.5 CONCLUSION AND OUTLOOK 491
ACKNOWLEDGMENTS 492
REFERENCES 492
13 DOMINO REACTIONS IN LIBRARY SYNTHESIS 497
VINCENT ESCHENBRENNER-LUX, HERBERT WALDMANN, AND KAMAL KUMAR
13.1 INTRODUCTION 497
13.2 DOMINO REACTIONS IN NATURAL-PRODUCT-INSPIRED COMPOUND COLLECTION
SYNTHESES 498
13.2.1 COINAGE METAL-CATALYZED DOMINO SYNTHESIS 498
13.2.2 MULTICATALYTIC DOMINO PROCESSES 500
13.2.3 SYNTHESIS OF NATURAL-PRODUCT-INSPIRED CENTROCOUNTINS USING DOMINO
REACTIONS 503
13.3 DOMINO APPROACHES TARGETING SCAFFOLD DIVERSITY 506
13.3.1 SUBSTRATE-BASED APPROACH: THE METATHESIS/METATHESIS DOMINO
PROCESS 507
13.3.2 REAGENT-BASED DOMINO APPROACHES 509
13.3.3 DOMINO REACTIONS IN THE BUILD-COUPLE-PAIR APPROACH FOR LIBRARY
SYNTHESIS 515
13.4 SOLID-PHASE DOMINO SYNTHESES OF COMPOUND COLLECTIONS 516
13.5 CONCLUSION 519
REFERENCES 520
14 DOMINO REACTIONS IN THE TOTAL SYNTHESIS OF NATURAL PRODUCTS 523
SVENIA-C. DIIFERT, JUDITH HIEROLD, AND LUTZ F. TIETZE
14.1 CATIONIC DOMINO REACTIONS 523
14.2 ANIONIC DOMINO REACTIONS 533
14.3 RADICAL DOMINO REACTIONS 549
14.4 PERICYCLIC DOMINO REACTIONS 551
14.5 TRANSITION-METAL-CATALYZED DOMINO REACTIONS 554
14.6 DOMINO REACTIONS INITIATED BY OXIDATION OR REDUCTION 568
14.7 CONCLUSION 571
REFERENCES 572
15 MULTICOMPONENT DOMINO PROCESS: RATIONAL DESIGN AND SERENDIPITY 579 '
QIAN WANG AND JIEPING ZHU
15.1 INTRODUCTION 579
15.2 BASIC CONSIDERATIONS OF MCRS 581
15.3 SUBSTRATE DESIGN APPROACH IN THE DEVELOPMENT OF NOVEL MCRS 583
15.3.1 CHEMISTRY OF A-ISOCYANOACETATES 583
15.3.2 FROM A-ISOCYANOACETATES TO A-ISOCYANOACETAMIDES 585
CONTENTS
I XI
15.3.3 FROM A-ISOCYANOACETAMIDES TO A-ISOCYANOACETIC ACIDS 589
15.3.4 BACK TO A-ISOCYANOACETATES 590
15.3.5 CHEMISTRY OF OXAZOLES 593
15.3.5.1 DIENOPHILE AS AN ADDITIONAL COMPONENT 593
15.3.5.2 USING DIENOPHILE-CONTAINING INPUTS 597
15.3.6 SERENDIPITY 6 01
15.3.6.1 GROEBKE-BLACKBURN-BIENAYME REACTION 601
15.3.6.2 ONE-CARBON OXIDATIVE HOMOLOGATION OF ALDEHYDES TO AMIDES 602
15.3.6.3 ONE-CARBON OXIDATIVE HOMOLOGATION OF ALDEHYDES TO
A-KETOAMIDES 604
15.4 CONCLUSION 607
REFERENCES 607
INDEX 611 |
| any_adam_object | 1 |
| author2 | Tietze, Lutz F. 1942- |
| author2_role | edt |
| author2_variant | l f t lf lft |
| author_GND | (DE-588)123655315 |
| author_facet | Tietze, Lutz F. 1942- |
| building | Verbundindex |
| bvnumber | BV041618775 |
| classification_rvk | VK 5500 VK 6000 |
| ctrlnum | (OCoLC)864546136 (DE-599)DNB103886089X |
| dewey-full | 547.2 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.2 |
| dewey-search | 547.2 |
| dewey-sort | 3547.2 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV041618775 |
| illustrated | Illustrated |
| indexdate | 2024-09-10T01:06:06Z |
| institution | BVB |
| isbn | 9783527334322 3527334327 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027059855 |
| oclc_num | 864546136 |
| open_access_boolean | |
| owner | DE-29T DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-29T DE-11 DE-19 DE-BY-UBM |
| physical | XXIII, 621 S. Ill. 244 mm x 170 mm |
| publishDate | 2014 |
| publishDateSearch | 2014 |
| publishDateSort | 2014 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Domino reactions concepts for efficient organic synthesis ed. by Lutz F. Tietze Weinheim Wiley-VCH 2014 XXIII, 621 S. Ill. 244 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Organische Synthese (DE-588)4075695-6 gnd rswk-swf Tandem-Reaktion (DE-588)4306783-9 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Tandem-Reaktion (DE-588)4306783-9 s Organische Synthese (DE-588)4075695-6 s DE-604 Tietze, Lutz F. 1942- (DE-588)123655315 edt X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4431084&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027059855&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Domino reactions concepts for efficient organic synthesis Organische Synthese (DE-588)4075695-6 gnd Tandem-Reaktion (DE-588)4306783-9 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4306783-9 (DE-588)4143413-4 |
| title | Domino reactions concepts for efficient organic synthesis |
| title_auth | Domino reactions concepts for efficient organic synthesis |
| title_exact_search | Domino reactions concepts for efficient organic synthesis |
| title_full | Domino reactions concepts for efficient organic synthesis ed. by Lutz F. Tietze |
| title_fullStr | Domino reactions concepts for efficient organic synthesis ed. by Lutz F. Tietze |
| title_full_unstemmed | Domino reactions concepts for efficient organic synthesis ed. by Lutz F. Tietze |
| title_short | Domino reactions |
| title_sort | domino reactions concepts for efficient organic synthesis |
| title_sub | concepts for efficient organic synthesis |
| topic | Organische Synthese (DE-588)4075695-6 gnd Tandem-Reaktion (DE-588)4306783-9 gnd |
| topic_facet | Organische Synthese Tandem-Reaktion Aufsatzsammlung |
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| work_keys_str_mv | AT tietzelutzf dominoreactionsconceptsforefficientorganicsynthesis |