Asymmetric dearomatization reactions:
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| Format: | Book |
| Language: | English |
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Weinheim
Wiley-VCH Verlag GmbH & Co. KGaA
[2016]
|
| Subjects: | |
| Online Access: | Verlag Inhaltsverzeichnis |
| Physical Description: | XIX, 399 Seiten Diagramme |
| ISBN: | 3527338519 9783527338511 9783527698479 |
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MARC
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| 245 | 1 | 0 | |a Asymmetric dearomatization reactions |c edited by Shu-Li You |
| 264 | 1 | |a Weinheim |b Wiley-VCH Verlag GmbH & Co. KGaA |c [2016] | |
| 264 | 4 | |c © 2016 | |
| 300 | |a XIX, 399 Seiten |b Diagramme | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
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| 653 | |a Catalysis | ||
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Drug Discovery & Development | ||
| 653 | |a Katalyse | ||
| 653 | |a Methods - Synthesis & Techniques | ||
| 653 | |a Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 653 | |a Wirkstoffforschung u. -entwicklung | ||
| 689 | 0 | 0 | |a Aromatische Verbindungen |0 (DE-588)4129374-5 |D s |
| 689 | 0 | 1 | |a Asymmetrische Reaktion |0 (DE-588)4143270-8 |D s |
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| 700 | 1 | |a You, Shu-Li |0 (DE-588)1111818886 |4 edt | |
| 710 | 2 | |a Wiley-VCH |0 (DE-588)16179388-5 |4 pbl | |
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Record in the Search Index
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| adam_text |
CONTENTS
YY
1.1
1.2
1.3
YY 4
2
2.1
2.2
2
.
2.1
2
.
2.2
2.2.3
2.3
2.4
2.4.1
2.4.2
2.4.3
2.5
2.5.1
2.5.2
2.5.3
2.6
UST OF CONTRIBUTORS XIII
PREFACE XVII
INTRODUCTION 1
WEIZHANG YYND5HU-LI YOU
WHY ASYMMETRIC DEAROMATIZATION REACTIONS? 1
DISCOVERY OF AROMATIC COMPOUNDS AND DEAROMATIZATION
REACTIONS 1
DEVELOPMENT OF DEAROMATIZATION REACTIONS 3
ASYMMETRIC DEAROMATIZATION REACTIONS 7
REFERENCES 8
ASYMMETRIC DEAROMATIZATION WITH CHYYRAL AUXILIARIES AND
REAGENTS 9
EIPETERKUNDIG
INTRODUCTION 9
CHIRAL .-BOUND AUXILIARIES 9
OXAZOLINES 9
IMINES, OXAZOLIDINES, AND HYDRAZONES 15
CHIRAL ETHERS AND AMINES 16
DIASTEREOSPECIFIC ANIONIC CYCLIZATIONS 20
USE OF CHIRAL REAGENTS 21
CHIRAL BASES IN DEAROMATIZING CYCLIZATIONS 21
CHIRAL NUCLEOPHILES 23
CHIRAL LIGANDS IN ENANTIOSELECTIVE NUCLEOPHILIC
ADDITIONS 23
CHIRAL YY-COMPLEXES 26
PLANAR CHIRAL YY6-YYYYYYYYYY COMPLEXES 26
YY6-YYYYYYYYYY COMPLEXES WITH A CNIRAL LIGAND 28
COMPLEXES WITH STEREOGENIC M
ETAL
YY
ENTERS 29
CONCLUSION 30
REFERENCES 30
3 ORGANOCATALYTIC ASYMMETRIC TRANSFER HYDROGENATION OF
(HETERO)ARENES 33
GAELLE MINGAT AND MAGNUS RUEPING
3.1 INTRODUCTION 33
3.2 ORGANOCATALYTIC ASYMMETRIC TRANSFER HYDROGENATION OF
HETEROAROMATICS 34
3.2.1 QUINOLINES 34
3.2.1.1 PR
00
F
0
YYFYYC
0
NCEPT 34
3.2.1.2 2YYSUBSTITUTED QUINOLINES 35
3.2.1.3 4-SUBSTITUTED QUINOLINES 40
3.2.1.4 3YYSUBSTITUTED QUINOLINES 41
3.2.1.5 2,3-DISUBSTITUTED QUINOLINES 42
3.2.1.6 YYYY/?/R.-TETRAHYDROQUINOLINES 45
3.2.2 BENZOXAZINES
YY
BENZOTHIAZINES
YY
AND BENZOXAZINONES 47
3.2.3 BENZODIAZEPINES AND BENZODIAZEPINONES 49
3.2.4 PYRIDINES 51
3.2.5 YYYY-INDOLES SI
3.2.6 QUINOXALINES AND QUINOXALINONES 52
3.3 ORGANOCATALYTIC ASYMMETRIC TRANSFER HYDROGENATION IN AQUEOUS
SOLUTION 53
3.4 CASCADE REACTIONS 54
3.4.1 INTRODUCTION 54
3.4.2 IN SITU GENERATION OF THE HETEROARENE 54
3.4.3 DEAROMATIZATION OF PYRIDINE/ASYMMETRIC YYYYYY-FRIEDEL-CRAFTS
ALKYLATION CASCADE 56
3.4.4 COMBINING PHOTOCHEMISTRY AND BROENSTED ACID CATALYSIS 57
3.4.4.1 QUINOLINES 57
3.4.4.2 PYRYLIUM IONS 58
3.5 COOPERATIVE AND RELAY CATALYSIS: COMBINING BROENSTED ACID- AND
METAL-CATALYSIS 59
3.5.1 INTRODUCTION 59
3.5.2 IMPROVEMENTS IN TRANSFER HYDROGENATION 60
3.5.2.1 REGENERABLE HYDROGEN SOURCES 60
3.5.2.2 ASYMMETRIC RELAY CATALYSIS (ARC) 62
3.5.3 COOPERATIVE METAL-BROENSTED ACID CATALYSIS 63
3.6 SUMMARY AND CONCLUSION 65
REFERENCES 66
4 TRANSITION-METAL-CATALYZED ASYMMETRIC HYDROGENATION OF
AROMATICS 69
RYOICHIKUWANO
4.1 INTRODUCTION 69
4.2 CATALYTIC ASYMMETRIC HYDROGENATION OF FIVE-MEMBERED
HETEROARENES 71
CATALYTIC ASYMMETRIC HYDROGENATION OF AZOLES AND INDOLES 71
4.2.1
4
.
9
.
11
4
9
1
9
4.2.1.3
49 14
49 9
4.2.3
4.3
4.3.1
4.3.1.1
4.3.1.2
4.3.2
4.3.2.1
4.3.2.2
4.3.2.3
4.3.2.4
4.3.2.5
4.3.2.6
4.3.2.7
4.3.3
4.4
4.4.1
4
4
?
4.5
5
5.1
5.2
5.2.1
5.2.2
5.2.3
5.2.4
5.2.5
5.2.6
RHODIUM-CATALYZED ASYMMETRIC HYDROGENATION OF INDOLES 71
RUTHENIUM-CATALYZED ASYMMETRIC HYDROGENATION OF AZOLES 73
PALLADIUM-CATALYZED ASYMMETRIC HYDROGENATION OF AZOLES 75
IRIDIUM-CATALYZED ASYMMETRIC HYDROGENATION OF INDOLES 77
CATALYTIC ASYMMETRIC HYDROGENATION OF OXYGEN-CONTAINING
HETEROARENES 77
CATALYTIC ASYMMETRIC HYDROGENATION OF SULFUR CONTAINING
HETEROARENES 79
CATALYTIC ASYMMETRIC HYDROGENATION OF SIXYYMEMBERED
HETEROARENES 79
CATALYTIC ASYMMETRIC HYDROGENATION OF AZINES
80
IRIDIUM-CATALYZED ASYMMETRIC HYDROGENATION OF PYRIDINES 80
IRIDIUM-CATALYZED ASYMMETRIC HYDROGENATION OF PYRIMIDINES 81
CATALYTIC ASYMMETRIC HYDROGENATION OF BENZO-FUSED AZINES 82
IRIDIUM-CATALYZED ASYMMETRIC HYDROGENATION OF QUINOLINES 82
RUTHENIUM-CATALYZED ASYMMETRIC HYDROGENATION OF
QUINOLINES
85
IRIDIUM-CATALYZED ASYMMETRIC HYDROGENATION OF ISOQUINOLINES 87
IRIDIUM-CATALYZED ASYMMETRIC HYDROGENATION OF QUINOXALINES 89
RUTHENIUM-CATALYZED ASYMMETRIC HYDROGENATION OF
QUINOXALINES 90
IRON-CATALYZED ASYMMETRIC HYDROGENATION OF QUINOXALINES 92
CATALYTIC ASYMMETRIC HYDROGENATION OF MISCELLANEOUS
SIXYYMEMBERED HETEROARENES 92
CATALYTIC ASYMMETRIC REDUCTION OF QUINOLINES WITH REDUCING
AGENTS OTHER YY
2
94
CATALYTIC ASYMMETRIC HYDROGENATION OF CARBOCYCLIC ARENES 95
RUTHENIUM-CATALYZED ASYMMETRIC HYDROGENATION OF CARBOCYCLES IN
BENZO-FUSEDHETEROARENES
96
RUTHENIUM-CATALYZED ASYMMETRIC HYDROGENATION OF
NAPHTHALENES 97
SUMMARY AND CONCLUSION 97
REFERENCES 98
STEPWISE ASYMMETRIC DEAROMATIZATION OF PHENOLS 103
QING GU
INTRODUCTION 103
STEPWISE ASYMMETRIC DEAROMATIZATION OF PHENOLS 103
ASYMMETRIC [4+2] REACTION 103
ASYMMETRIC HECK REACTION 106
ASYMMETRIC (HETERO) MICHAEL REACTION 108
ASYMMETRIC STETTER REACTION 119
ASYMMETRIC RAUHUT-CURRIER REACTION 120
ASYMMETRIC L,6YYDIENYYNE CYCLIZED REACTION 122
6.3
6.3.1
6.3.2
6.4
ASYMMETRIC OXIDATIVE DEAROMATIZATION REACTION 129
MUHAMMET YYYYYYYYYYYYYY AND KAZUAKI ISHIHARA
INTRODUCTION 129
DIASTEREOSELECTIVE OXIDATIVE DEAROMATIZATION USING CHIRAL
AUXILIARIES 129
ENANTIOSELECTIVE OXIDATIVE DEAROMATIZATION USING CHIRAL REAGENTS
OR CATALYSTS 132
CHIRAL TRANSITION METAL COMPLEXES 132
CHIRAL HYPERVALENT IODINES(III
YY
V) AND HYPOIODITES(I) 139
CONCLUSIONS AND PERSPECTIVES 148
REFERENCES 149
7 ASYMMETRIC DEAROMATIZATION VIA CYCLOADDITION REACTION 153
SARAH E. REISMAN, YY\AADEYYE\NE E. KIEFFER, AND HAOXUAN WANG
7.1 INTRODUCTION 153
7.2 [2 + 1] CYCLOADDITION 153
7.2.1 ASYMMETRIC BUCNNER REACTION 153
7.2.2 CYCLOPROPANATION OF HETEROCYCLIC COMPOUNDS ISS
7.3 [3 + 2] CYCLOADDITION 156
7.4 [3 + 3] CYCLOADDITION 161
7.5 [4 + 2] CYCLOADDITION 163
7.6 [4 + 3] CYCLOADDITION 170
7.7 CONCLUSION 173
REFERENCES 173
8 ORGANOCATALYTIC ASYMMETRIC DEAROMATIZATION REACTIONS 175
SUSANA S. LOPEZ, SN K. NIMMAGADDA, AND JON C. ANTULA
S
I INTRODUCTION 175
8.2 DIELS-ALDER 175
8.3 OXIDATIVE DEAROMATIZATION 179
8.4 CASCADE REACTIONS 186
8.5 STEPWISE 193
8.6 NUCLEOPHILIC DEAROMATIZATION 200
8.7 SUMMARY AND CONCLUSION 204
REFERENCES 205
9 DEAROMATIZATION VIA TRANSITION-METAL-CATALYZED ALLYLIC SUBSTITUTION
REACTIONS 207
TETSUHIRO NEMOTO ARID YASUMASA HAMADA
9.1 INTRODUCTION 207
9.2 DEAROMATIZATION OF INDOLES AND PYRROLES VIA TRANSITION-METAL-
CATALYZED ALLYLIC SUBSTITUTION REACTIONS 208
5.3 CONCLUSION AND PERSPECTIVE 126
REFERENCES 127
6
.1
6.2
9.3
9.4
9.5
10
10.1
10.2
10.3
10.4
11
11.1
11.2
11
.
2.1
11
.
2
.
1.1
11
.
2
.
1.2
11.2.1.3
119.-1-4
11.2.1.5
11
.
2
.
1.6
11
.
2.2
11
.
2
.
2.1
11
.
2
.
2.2
11.2.2.3
11.2.2.4
11.2.2.5
11.2.3
11.2.3.1
11.2.3.2
11.2.3.3
11.2.4
11.3
DEAROMATIZATION OF PHENOLS VIA TRANSITION-METAL-CATALYZED ALLYLIC
SUBSTITUTION REACTIONS 21YY
DEAROMATIZATION OT PHENOLS AND INDOLES VIA ACTIVATION OFPROPARGYL
CARBONATES WITH PD CATALYST 221
CONCLUSION 226
REFERENCES 226
DEAROMATIZATION VIA TRANSITION-METAL-CATALYZED CROSS-COUPLING
REACTIONS 229
R
0
B\N B. BEDFORD
INTRODUCTION: FROM CROSS-COUPLING TO CATALYTIC
DEAROMATIZATION 229
DEAROMATIZATION OF PHENOLIC SUBSTRATES 231
DEAROMATIZATION OF NITROGEN-CONTAINING SUBSTRATES 240
CONCLUSION AND
O
N
TLO
O
K
244
REFERENCES 245
DEAROMATIZATION REACTIONS OF ELECTRON-DEFICIENT AROMATIC
2
4
7
YY
YY
\\\
YYYY
CHIHIRO TSUKANO AND YOSHIJI TAKEMOTO
INTRODUCTION 247
DEAROMATIZATION OF ACTIVATED PYRIDINES AND OTHER
ELECTRON-DEFICIENT HETEROCYCLES 248
DEAROMATIZATION VIA ALKYL PYRIDINIUM SALTS 248
REDUCTION WITH BOROHYDRIDES 248
REDUCTION WITH NA2S
2
YY
4
249
REDUCTION WITH OTHER REDUCING AGENTS 250
NUCLEOPHILIC ADDITION OF GRIGNARD REAGENTS 251
NUCLEOPHILIC ADDITION OF CYANIDE 252
ADDITION OF OTHER CARBON NUCLEOPHILES 252
DEAROMATIZATION VIA ALKOXYCARBONYLPYRIDINIUM
SALTS 253
REDUCTION WITH HYDRIDE NUCLEOPHILES 254
ADDITION OF METAL NUCLEOPHILES
YY
INCLUDING GRIGNARD
REAGENTS 255
ADDITION OF ENOLATES AND RELATED CARBON NUCLEOPHILES 261
NUCLEOPHILIC ADDITION OF CYANIDE 264
ADDITION OF OTHER NUCLEOPHILES 265
DEAROMATIZATION VIA ACYL PYRIDINIUM SALTS 266
REDUCTION WITH HYDRIDE REDUCING AGENTS 266
ADDITION OF METAL NUCLEOPHILES INCLUDING GRIGNARD REAGENTS 269
ADDITION OF ENOLATES AND RELATED CARBON NUCLEOPHILES 270
DEAROMATIZATION THROUGH OTHER PYRIDINIUM CATIONS 270
SUMMARY AND CONCLUSION 274
REFERENCES 274
12
12.1
12.2
12
.
2.1
12
.
2.2
12.2.3
12.2.3.1
12.2.3.2
12.2.3.3
12.2.3.4
12.2.3.5
12.2.3.6
12.2.3.7
1
9
.
9
4
12.2.5
12.2.5.1
12.2.5.2
12.2.5.3
12.2.5.4
12.2.5.5
12.2.5.6
12
.
2.6
12.2.7
12
.
2.8
12.3
12.4
12.5
13
13.1
13.2
13.2.1
13.2.2
13.2.3
13.2.4
13.3
13.4
ASYMMETRIC DEAROMATIZATION UNDER ENZYMATIC CONDITIONS 279
S\M0N E. LEWIS
INTRODUCTION 279
DEAROMATIZING ARENE C/S-DIHYDROXYLATION 280
EARLY DEVELOPMENT 280
TYPES OF ARENE DIOXYGENASE 281
SUBSTRATE SCOPE AND REGIOSELECTIVITY 283
MONOCYCLIC SUBSTITUTED BENZENE SUBSTRATES (EXCLUDING BIARYLS) 299
BIARYL SUBSTRATES 299
NAPHTHALENE SUBSTRATES 299
BENZOIC ACID SUBSTRATES 299
HETEROCYCLIC SUBSTRATES (MONO- AND BICYCLIC) 300
BICYCLIC CARBOCYCLIC SUBSTRATES (OTHER THAN NAPHTHALENES) 300
TRICYCLIC SUBSTRATES (CARBO- AND HETEROCYCLIC) 300
AVAILABILITY OF ARENE A
YY
5YYDIOLS 300
USES IN SYNTHESIS 302
TOTAL SYNTHESIS 302
PHARMACEUTICALS AND AGROCHEMICALS 315
POLYMERS 317
FLAVORS AND FRAGRANCES 320
DYES 321
LIGANDS AND MOFS 321
INCREASING THE SUBSTRATE SCOPE 324
ACCESSING BOTH ENANTIOMERIC SERIES 326
IMPROVEMENTS TO THE PRODUCTION PROCESS 328
DEAROMATIZING ARENE EPOXIDATION 328
DEAROMATIZING ARENE REDUCTION 330
SUMMARY AND CONCLUSION 330
LIST OF ABBREVIATIONS 331
REFERENCES 332
TOTAL SYNTHESIS OF COMPLEX NATURAL PRODUCTS VIA
DEAROMATIZATION 347
WEIQMG XIE AND DAWEI YY\AA
INTRODUCTION 347
NATURAL PRODUCTS SYNTHESIS VIA OXIDATIVE DEAROMATIZATION 348
ENZYMATIC DIHYDROXYLATIVE DEAROMATIZATION OF ARENE 348
OXIDATIVE DEAROMATIZATION OF PHENOL 349
OXIDATIVE CYCLOISOMERIZATION REACTION OF PHENOL 355
OXIDATIVE DEAROMATIZATION OF INDOLE IN SYNTHESIS OF NATURAL
PRODUCTS 357
DEAROMATIZATION VIA CYCLOADDITION IN SYNTHESIS OF NATURAL
PRODUCTS 360
DEAROMATIZATION VIA NUCLEOPHILIC ADDITION IN SYNTHESIS OF NATURAL
PRODUCTS 367
13.5 REDUCTIVE DEAROMATIZATION IN SYNTHESIS OF NATURAL PRODUCTS 367
13.6 DEAROMATIZATION VIA ELECTROPHILIC ADDITION IN SYNTHESIS OF NATURAL
PRODUCTS YY
13.7 DEAROMATIZATION VIA INTRAMOLECULAR ARYLATION IN NATURAL PRODUCTS
SYNTHESIS 371
13.8 SUMMARY AND PERSPECTIVE 373
REFERENCES 374
14 MISCELLANEOUS ASYMMETRIC DEAROMATIZATION REACTIONS 379
WEIZHORIG ANDSHU-LI YOU
14.1 INTRODUCTION 379
14.2 MISCELLANEOUS ASYMMETRIC DEAROMATIZATION REACTIONS 379
14.3 CONCLUSIONS AND PERSPECTIVES 388
REFERENCES 388
INDEX 391 |
| any_adam_object | 1 |
| author2 | You, Shu-Li |
| author2_role | edt |
| author2_variant | s l y sly |
| author_GND | (DE-588)1111818886 |
| author_facet | You, Shu-Li |
| building | Verbundindex |
| bvnumber | BV043654043 |
| classification_rvk | VK 5800 VK 6000 |
| ctrlnum | (OCoLC)964453787 (DE-599)DNB1084599309 |
| dewey-full | 540 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences |
| dewey-raw | 540 |
| dewey-search | 540 |
| dewey-sort | 3540 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| id | DE-604.BV043654043 |
| illustrated | Not Illustrated |
| indexdate | 2025-03-10T15:04:14Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 3527338519 9783527338511 9783527698479 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-029067580 |
| oclc_num | 964453787 |
| open_access_boolean | |
| owner | DE-703 DE-11 DE-19 DE-BY-UBM DE-83 |
| owner_facet | DE-703 DE-11 DE-19 DE-BY-UBM DE-83 |
| physical | XIX, 399 Seiten Diagramme |
| publishDate | 2016 |
| publishDateSearch | 2016 |
| publishDateSort | 2016 |
| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spelling | Asymmetric dearomatization reactions edited by Shu-Li You Weinheim Wiley-VCH Verlag GmbH & Co. KGaA [2016] © 2016 XIX, 399 Seiten Diagramme txt rdacontent n rdamedia nc rdacarrier Asymmetrische Reaktion (DE-588)4143270-8 gnd rswk-swf Aromatische Verbindungen (DE-588)4129374-5 gnd rswk-swf Catalysis Chemie Chemistry Drug Discovery & Development Katalyse Methods - Synthesis & Techniques Organische Chemie / Methoden, Synthesen, Verfahren Wirkstoffforschung u. -entwicklung Aromatische Verbindungen (DE-588)4129374-5 s Asymmetrische Reaktion (DE-588)4143270-8 s DE-604 You, Shu-Li (DE-588)1111818886 edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, EPUB 978-3-527-69848-6 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-69849-3 Erscheint auch als Online-Ausgabe, PDF 978-3-527-69846-2 http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33851-1/ Verlag DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029067580&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Asymmetric dearomatization reactions Asymmetrische Reaktion (DE-588)4143270-8 gnd Aromatische Verbindungen (DE-588)4129374-5 gnd |
| subject_GND | (DE-588)4143270-8 (DE-588)4129374-5 |
| title | Asymmetric dearomatization reactions |
| title_auth | Asymmetric dearomatization reactions |
| title_exact_search | Asymmetric dearomatization reactions |
| title_full | Asymmetric dearomatization reactions edited by Shu-Li You |
| title_fullStr | Asymmetric dearomatization reactions edited by Shu-Li You |
| title_full_unstemmed | Asymmetric dearomatization reactions edited by Shu-Li You |
| title_short | Asymmetric dearomatization reactions |
| title_sort | asymmetric dearomatization reactions |
| topic | Asymmetrische Reaktion (DE-588)4143270-8 gnd Aromatische Verbindungen (DE-588)4129374-5 gnd |
| topic_facet | Asymmetrische Reaktion Aromatische Verbindungen |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33851-1/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029067580&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT youshuli asymmetricdearomatizationreactions AT wileyvch asymmetricdearomatizationreactions |