Handbook of metathesis: 2 Applications in organic synthesis
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2015
|
| Ausgabe: | 2. ed. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXVI, 743 S. graph. Darst. |
| ISBN: | 9783527339495 |
Internformat
MARC
| LEADER | 00000nam a2200000 cc4500 | ||
|---|---|---|---|
| 001 | BV042407321 | ||
| 003 | DE-604 | ||
| 005 | 20151020 | ||
| 007 | t | ||
| 008 | 150313s2015 d||| |||| 00||| eng d | ||
| 020 | |a 9783527339495 |c print |9 978-3-527-33949-5 | ||
| 035 | |a (OCoLC)909801371 | ||
| 035 | |a (DE-599)BVBBV042407321 | ||
| 040 | |a DE-604 |b ger |e rakwb | ||
| 041 | 0 | |a eng | |
| 049 | |a DE-11 |a DE-703 |a DE-29T |a DE-19 | ||
| 084 | |a VK 6000 |0 (DE-625)147413:253 |2 rvk | ||
| 245 | 1 | 0 | |a Handbook of metathesis |n 2 |p Applications in organic synthesis |c ed. by Robert H. Grubbs ... |
| 250 | |a 2. ed. | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2015 | |
| 300 | |a XXVI, 743 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Organische Synthese |0 (DE-588)4075695-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Metathese |g Chemie |0 (DE-588)4169656-6 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Metathese |g Chemie |0 (DE-588)4169656-6 |D s |
| 689 | 0 | 1 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Grubbs, Robert H. |d 1942-2021 |0 (DE-588)124993532 |4 edt | |
| 773 | 0 | 8 | |w (DE-604)BV025307693 |g 2 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-69404-4 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, MOBI |z 978-3-527-69403-7 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-69402-0 |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027842890&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-027842890 | ||
Datensatz im Suchindex
| _version_ | 1804153066087251968 |
|---|---|
| adam_text | CONTENTS
PREFACE XV
LIST OF CONTRIBUTORS XVII
LIST OF ABBREVIATIONS XXI
1 GENERAL RING-CLOSING METATHESIS 1
PAUL R. HANSON, SOMA MAITRA, RAMBABU CHEGONDI, ANDJANA L. MARKLEY
1.1 INTRODUCTION 1
1.2 CARBOCYCLES (INTRODUCTION) 3
1.2.1 SMALL-SIZED CARBOCYCLES 3
1.2.2 MEDIUM-SIZED CARBOCYCLES 9
1.2.3 SPIRO CARBOCYCLES 20
1.3 SYNTHESIS OF BRIDGED BICYCLOALKENES 25
1.4 SYNTHESIS OF HETEROCYCLES CONTAINING SI, P, S, OR B 29
1.4.1 SI-HETEROCYCLES 29
1.4.2 P-HETEROCYCLES 34
1.4.3 S-HETEROCYCLES 42
1.4.4 B-HETEROCYCLES 46
1.5 SYNTHESIS OF O-HETEROCYCLES 51
1.5.1 SMALL AND MEDIUM-SIZE CYCLIC ETHERS 51
1.5.2 POLYCYCLIC ETHERS 59
1.6 SYNTHESIS OF N-HETEROCYCLES 63
1.6.1 N-HETEROCYCLES 63
1.6.2 SMALL AND MEDIUM-SIZED LACTAMS 73
1.7 SYNTHESIS OF CYCLIC CONJUGATED DIENES 77
1.8 ALKYNE METATHESIS
86
1.9 ENYNE METATHESIS 89
1.9.1 GENERAL ENYNE METATHESIS 90
1.9.2 DIENYNE METATHESIS 93
1.10 TANDEM PROCESSES 93
1.10.1 TANDEM ROM/RCM 98
1.10.2 OTHER TANDEM RCMS 103
1.11 SYNTHESIS OF MACROCYCLES 105
1.11.1 MACROCYCLES 105
HTTP://D-NB.INFO/1063375657
VI
CONTENTS
1.11.2 MACROLACTONES 110
1.11.3 MACROLACTAMS 126
1.12 RCM AND ISOMERIZATION VIA RU-H 147
1.13 RELAY RCM (RRCM) 149
1.14 Z-SELECTIVE RCM 15S
1.14.1 SUBSTRATE-CONTROLLED Z-SELECTIVE RCM 1S5
1.14.2 CATALYST-CONTROLLED Z-SELECTIVE RCM 155
1.15 ENANTIOSELECTIVE RCM 158
1.16 CONCLUSION 161
ACKNOWLEDGMENTS 162
REFERENCES 162
2 CROSS-METATHESIS 171
DANIEL J. O LEARYAND GREGORY W. O NEIL
2.1 EARLY EXAMPLES USING WELL-DEFINED MOLYBDENUM AND RUTHENIUM
CATALYSTS 171
2.2 THE GENERAL MODEL FOR SELECTIVITY IN CM REACTIONS 172
2.3 DEFINITION OF CROSS-METATHESIS REACTION CATEGORIES AND CHAPTER
ORGANIZATION 176
2.4 HYDROCARBONS 177
2.4.1 ALKANE EXTENSIONS 177
2.4.2 UNSATURATED HYDROCARBONS, INCLUDING STYRENE 182
2.4.3 ETHYLENE CROSS-METATHESIS 188
2.5 BORON 188
2.6 NITROGEN 195
2.6.1 AMINES 195
2.6.2 AMINES AS CM PARTNERS IN HETEROCYCLE SYNTHESES 198
2.6.3 ACRYLONITRILE AND OTHER NITRILE-BASED CM APPLICATIONS 202
2.6.4 OTHER NITROGENOUS SUBSTRATES 203
2.7 OXYGEN 205
2.7.1 PRIMARY ALLYLIC ALCOHOLS AND DERIVATIVES 205
2.7.2 SECONDARY ALLYLIC ALCOHOLS AND DERIVATIVES 209
2.7.3 TERTIARY ALLYLIC ALCOHOLS AND DERIVATIVES 213
2.7 A HOMOALLYLIC ALCOHOLS AND DERIVATIVES 215
2.7.5 VINYL ETHERS 216
2.7.6 ACROLEIN, CROTONALDEHYDE, AND METHACROLEIN 218
2.7.7 METHYL VINYL KETONE AND RELATED SYSTEMS 224
2.7.8 ACRYLIC ACID 230
2.7.9 ACRYLIC ACID DERIVATIVES, INCLUDING ESTERS, THIOESTERS, AND
AMIDES 232
2.8 HALIDES 247
2.9 PHOSPHORUS 252
2.10 SULFUR 2SS
2.11 FRAGMENT COUPLING REACTIONS 257
2.11.1 ACETOGENINS 258
CONTENTS
VII
2.11.2 CROSS-METATHESIS SELECTIVITY 262
2.11.3 TUNING METATHESIS SELECTIVITY 267
2.11.4 CM AS AN ALTERNATIVE COUPLING STRATEGY 269
2.11.5 CM-BASED ANALOG SYNTHESIS 271
2.11.6 POLYENE METATHESIS 273
2.11.7 CROSS-METATHESIS REACTION OPTIMIZATION: PINNAIC ACID 275
2.12 CONCLUSIONS 280
REFERENCES 282
3 VIGNETTE: EXTENDING THE APPLICATION OF METATHESIS IN CHEMICAL
BIOLOGY - THE DEVELOPMENT OF SITE-SELECTIVE PEPTIDE AND PROTEIN
MODIFICATIONS 295
YUYA A. LIN AND BENJAMIN G. DAVIS
3.1 INTRODUCTION 295
3.2 CROSS-METATHESIS METHODOLOGY STUDIES IN AQUEOUS MEDIA 296
3.2.1 ALLYL SULFIDES ARE REACTIVE SUBSTRATES IN OLEFIN METATHESIS 296
3.2.2 SULFUR-RELAYED CROSS-METATHESIS 297
3.2.3 APPLICATION OF AQUEOUS METATHESIS OF ALLYL SULFIDES IN
SYNTHESIS 300
3.2.4 CROSS-METATHESIS OF SE-ALLYL SELENOCYSTEINE 300
3.3 STRATEGIES FOR ALLYL CHALOGENIDE INCORPORATION INTO PROTEINS 301
3.3.1 CONJUGATE ADDITION TO DEHYDROALANINE 302
3.3.2 ALLYL SELENENYLSULFIDE REARRANGEMENT 302
3.3.3 S-ALLYL CYSTEINE AS A METHIONINE SURROGATE 303
3.3.4 OTHER GENETIC INCORPORATION STRATEGIES 303
3.4 OLEFIN METATHESIS ON PROTEINS 304
3.4.1 MAGNESIUM(II) IS AN ESSENTIAL ADDITIVE IN OLEFIN METATHESIS
ON PROTEINS 304
3.4.2 FURTHER INVESTIGATION OF ALLYL ETHERS AND ALLYL SULFIDES IN RCM
OF PROTEINS AND PEPTIDES 304
3.4.3 EXPANDING THE SCOPE OF CROSS-METATHESIS ON PROTEINS 306
3.5 OUTLOOK 307
REFERENCES 307
4 RUTHENIUM-CATALYZED TANDEM METATHESIS/NON-METATHESIS
PROCESSES 311
YOUN H. NAM AND MARC L. SNAPPER
4.1 INTRODUCTION 311
4.2 METATHESIS/ISOMERIZATION 311
4.2.1 RCM/ISOMERIZATION 311
4.2.2 ISOMERIZATION/RCM 322
4.2.3 CM/ISOMERIZATION 325
4.2.4 ENYNE METATHESIS/ISOMERIZATION 327
4.2.5 ISOMERIZATION/ENYNE METATHESIS 329
4.3 METATHESIS/HYDROGENATION 329
VIII
CONTENTS
4.3.1 RCM/HYDROGENATION 329
4.3.2 CM/HYDROGENATION 336
4.4 METATHESIS/OXIDATION 338
4.4.1 RCM/OXIDATIVE AROMATIZATION 338
4.4.2 RCM/ALLYLIC OXIDATION 342
4.4.3 METATHESIS/HYDROXYLATION 343
4.5 METATHESIS/CYCLIZATION 348
4.5.1 CM/AZA-MICHAEL REACTION 348
4.5.2 CM/OXA-MICHAEL REACTION 353
4.5.3 CM/CONJUGATE ADDITION 357
4.5.4 CM/CONJUGATE ADDITION/CYCLIZATION 360
4.5.5 RCM/ISOMERIZATION/CYCLIZATION 360
4.6 METATHESIS/ATOM-TRANSFER RADICAL ADDITION 362
4.6.1 RCM/KHARASCH ADDITION 363
4.6.2 CM/KHARASCH ADDITION 366
4.6.3 ENYNE METATHESIS/KHARASCH ADDITION 368
4.7 METATHESIS/REARRANGEMENT 368
4.7.1 CLAISEN REARRANGEMENT/RCM 368
4.8 METATHESIS/CYCLOPROPANATION 370
4.8.1 CYCLOPROPANATION/RCM 370
4.8.2 ENYNE METATHESIS/CYCLOPROPANATION 371
4.8.3 CM/CYCLOPROPANATION 372
4.8.4 RCM/ISOMERIZATION/CYCLOPROPANATION 372
4.9 METATHESIS/MISCELLANEOUS 373
4.9.1 CM/WITTIG OLEFINATION 373
4.9.2 CM/CYCLOADDITION (HETERO-PAUSON-KHAND REACTION) 374
4.9.3 ENYNE METATHESIS/HYDROVINYLATION 375
4.9.4 ALLYLIC CARBOXYLATION/RCM 375
4.10 CONCLUSIONS 376
REFERENCES 377
5 ENYNE METATHESIS 381
JINGWEI LI AND DAESUNG LEE
5.1 INTRODUCTION 381
5.2 ENYNE METATHESIS 382
5.2.1 BRIEF HISTORICAL BACKGROUND (1985-2002) 382
5.2.2 MECHANISTIC STUDIES AND SELECTIVITY ISSUES 384
5.2.2.1 DICHOTOMY OF MECHANISM - ENE-FIRST OR YNE-FIRST 384
5.2.2.2 REGIOSELECTIVITY IN ENYNE RING-CLOSING METATHESIS 388
5.2.2.3 REGIO AND STEREOSELECTIVITY IN ENYNE CROSS METATHESIS 391
5.2.3 ENYNE METATHESIS AND METALLOTROPIC [1, 3] SHIFT (M&M) 395
5.2.4 OTHER METAL-CATALYZED ENYNE METATHESES (SKELETAL
REORGANIZATIONS) 399
5.2.4.1 INTRODUCTION 399
5.2.4.2 FORMATION OF TYPE-1 EXO PRODUCTS 400
CONTENTS
I IX
5.2.4.3 FORMATION OF TYPE-II EXO PRODUCTS 400
5.2.4.4 FORMATION OF ENDO PRODUCTS 403
5.2.4.5 MISCELLANEOUS 404
5.3 STRATEGIC APPLICATION OF ENYNE METATHESIS IN ORGANIC SYNTHESIS 405
5.3.1 ENYNE METATHESIS 405
5.3.1.1 ENYNE RCM IN SYNTHESIS OF CARBOCYCLES AND HETEROCYCLES 405
5.3.1.2 ENYNE CM 410
5.3.1.3 ENYNE METATHESIS IN NATURAL PRODUCTS SYNTHESIS 412
5.3.2 TANDEM ENYNE METATHESIS 415
5.3.2.1 DIENYNE METATHESIS 417
5.3.2.2 ENYNE RCM-CM SEQUENCE 425
5.3.2.3 ENYNE RING-REARRANGEMENT METATHESIS (RRM) 427
5.3.2.4 MULTIPLE ENYNE METATHESIS 430
5.3.2.5 ENYNE CM-RCM SEQUENCE 431
5.3.3 TANDEM ENYNE METATHESIS-DIELS-ALDER REACTION SEQUENCES 432
5.3.3.1 ENYNE METATHESIS-INTERMOLECULAR DIELS- ALDER REACTION 432
5.3.3.2 ENYNE METATHESIS-INTRAMOLECULAR DIELS-ALDER REACTION 436
5.3.4 OTHER TANDEM ENYNE METATHESIS SEQUENCES 437
5.4 PERSPECTIVE 438
REFERENCES 439
6 ALKYNE METATHESIS 445
ALOIS FURS
TRIER
6.1 INTRODUCTION 445
6.2 BACKGROUND INFORMATION 445
6.3 MOLYBDENUM ALKYLIDYNE CATALYSTS WITH SILANOLATE LIGANDS 450
6.3.1 GENERAL 450
6.3.2 REPRESENTATIVE PROCEDURE: RING-CLOSING ALKYNE METATHESIS WITH THE
AID OF A BENCH-STABLE MOLYBDENUM ALKYLIDYNE ADDUCT 453
6.3.3 MOLYBDENUM NITRIDES AS PRECATALYSTS 454
6.3.4 STRUCTURAL AND MECHANISTIC ASPECTS 455
6.4 OTHER CATALYTICALLY ACTIVE MOLYBDENUM ALKYLIDYNE COMPLEXES 458
6.5 NOVEL TUNGSTEN ALKYLIDYNE CATALYSTS 461
6.6 BASIC TYPES OF APPLICATIONS 462
6.6.1 ALKYNE SELF-METATHESIS AND CYCLO-OLIGOMERIZATION REACTIONS 462
6.6.2 OLIGOMERIZATION AND POLYMERIZATION REACTIONS 465
6.6.3 ALKYNE CROSS METATHESIS 468
6.6.4 RING-CLOSING ALKYNE METATHESIS 470
6.6.5 METATHESIS OF TERMINAL ALKYNES 472
6.7 SELECTED APPLICATIONS 474
6.7.1 ORGANOMETALLIC SUBSTRATES 474
6.7.2 OLFACTORY MACROCYCLES 475
6.7.3 CRUENTAREN A 476
6.7.4 HALICLONACYCLAMINE C 477
6.7.5 NAKADOMARIN A 478
X
CONTENTS
6.7.6 PROSTAGLANDINS AND OXYLIPINS 478
6.7.7 NEURYMENOLIDE A 481
6.7.8 TULEARIN C 482
6.7.9 STEREOSELECTIVE SYNTHESES OF 1,3-DIENES BY RCAM/SEMIREDUCTION:
TOTAL SYNTHESES OF LATRUNCULIN, LACTIMIDOMYCIN, AND
LEIODERMATOLIDE
483
6.7.10 AMPHIDINOLIDE V 488
6.7.11 CITREOFURAN 489
6.7.12 POLYCAVERNOSIDE A 490
6.7.13 AMPHIDINOLIDE F 491
6.7.14 SPIRASTRELLOLIDE F 493
6.8 CONCLUSIONS 493
REFERENCES 495
7 CATALYST-CONTROLLED STEREOSELECTIVE OLEFIN METATHESIS 503
AMIRH. HOVEYDA, R. KASHIFM. KHAN, SEBASTIAN TORKER, AND
STEVEN J. MALCOLMSON
7.1 INTRODUCTION 503
1.1 ENANTIOSELECTIVE RING-OPENING/CROSS-METATHESIS (EROCM) 504
7.2.1 REACTIONS WITH CHIRAL RU CARBENES 504
7.2.2 REACTIONS WITH CHIRAL MO-BASED BIPHENOLATES 509
7.2.3 REACTIONS OF AZABICYCLES: RU- VERSUS MO-BASED CATALYSTS 509
7.2.4 APPLICATION TO ENANTIOSELECTIVE SYNTHESIS OF A NATURAL PRODUCT 512
7.3 ENANTIOSELECTIVE RING-OPENING/RING-CLOSING METATHESIS
(ERORCM) 512
7.4 ENANTIOSELECTIVE RING-CLOSING METATHESIS (ERCM) 514
7.4.1 REACTIONS WITH CHIRAL RU-BASED COMPLEXES 514
7.4.2 ERCM REACTIONS WITH CHIRAL MO-BASED DIOLATES 516
7.4.2.1 SYNTHESIS OF AF-HETEROCYCLES 516
7.4.2.2 SYNTHESIS OF CYCLIC ALKENYL ETHERS 519
7.4.2.3 SYNTHESIS OF CYCLIC ALKENES WITH A P-STEREOGENIC CENTER 520
7.4.2.4 CONTROL OF PLANAR STEREOGENICITY 520
7.4.3 REACTIONS WITH MONOPYRROLIDE-ARYLOXIDE (MAP) STEREOGENIC-AT-MO
COMPLEXES 520
7.4.3.1 CATALYST DESIGN, ERCM REACTIONS, AND APPLICATION TO TOTAL
SYNTHESIS OF QUEBRACHAMINE 520
7.4.3.2 ENANTIOSELECTIVE ENYNE RCM 525
7.5 Z-SELECTIVE OLEFIN METATHESIS REACTIONS WITH MO- AND W-BASED
COMPLEXES 526
7.5.1 REACTIONS WITH CHIRAL MO-BASED DIOLATES: NET ENANTIO- AND
Z-SELECTIVE CROSS-METATHESIS (CM) 526
7.5.2 REACTIONS WITH MO- AND W-BASED MONOPYRROLIDE ARYLOXIDE
(MAP) COMPLEXES 528
7.5.2.1 CATALYTIC ENANTIO- AND Z-SELECTIVE RING-OPENING/CROSS-METATHESIS
(ROCM) 528
CONTENTS
I XI
7.5.2.2 CATALYTIC Z-SELECTIVE HOMO-COUPLING 531
7.5.2.3 CATALYTIC Z-SELECTIVE CROSS-METATHESIS (CM) 532
7.5.2.4 PURE -ALKENES BY CATALYTIC Z-SELECTIVE ETHENOLYSIS 540
7.5.2.5 CATALYTIC Z-SELECTIVE MACROCYCLIC RING-CLOSING METATHESIS
(RCM) 540
7.6 Z-SELECTIVE OLEFIN METATHESIS REACTIONS WITH RU COMPLEXES 545
7.6.1 REACTIONS WITH COMPLEXES CONTAINING A BIDENTATE A/-HETEROCYCLIC
CARBENE (NHC) LIGAND 545
7.6.1.1 HOMO-COUPLING REACTIONS 545
7.6.1.2 CROSS-METATHESIS (CM) REACTIONS 546
7.6.1.3 RING-CLOSING METATHESIS (RCM) REACTIONS 547
7.6.1.4 RING-OPENING/CROSS-METATHESIS (ROCM) REACTIONS 548
7.6.2 REACTIONS WITH RU COMPLEXES CONTAINING A DITHIOLATE LIGAND 550
7.6.2.1 CATALYST DESIGN AND SYNTHESIS 550
7.6.2.7 RING-OPENING/CROSS-METATHESIS (ROCM) REACTIONS 551
7.7 Z-SELECTIVE RING-OPENING METATHESIS POLYMERIZATION 552
7.7.1 REACTIONS WITH MO-AND W-BASED COMPLEXES 552
7.7.2 REACTIONS WITH RU-BASED CARBENES 555
7.7.2.1 PHOSPHINE-CONTAINING COMPLEXES 555
7.7.2.2 NHC-CONTAINING COMPLEXES 555
7.8 CONCLUSIONS AND OUTLOOK 556
ACKNOWLEDGMENTS 558
REFERENCES 559
8 TWO VIGNETTES: RCM IN NATURAL PRODUCT TOTAL SYNTHESIS 563
CHRISTOPHER D. VANDERWAL, MADE] A. WALCZAK, AND SAMUEL J. DANISHEFSKY
8.1 VIGNETTE 1: ALLYLSILANE RCM/ELECTROPHILIC DESILYLATION AS A MEANS TO
ACCESS RINGS WITH EXOCYCLIC ALKENES 563
CHRISTOPHER D. VANDERWAL
8.2 VIGNETTE 2: SYNTHESIS OF ANTIMETASTATIC AGENTS USING RING-CLOSING
METATHESIS 574
MACIEJA. WALCZAK AND SAMUEL J. DANISHEFSKY
REFERENCES 581
9 METATHESIS OF SILICON-CONTAINING OLEFINS 583
CEZARY PIETRASZUK, PIOTR PAWLUC, AND BOGDAN MARCINIEC
9.1 INTRODUCTION 5 83
9.2 HOMO AND CROSS-METATHESIS VERSUS SILYLATIVE COUPLING OF
VINYLSILICON COMPOUNDS 584
9.3 HOMOMETATHESIS OF ALLYLSILANES AND THEIR CROSS-METATHESIS WITH
OLEFINS 594
9.4 SILYLATIVE COUPLING VERSUS CROSS-METATHESIS OF VINYLSILANES IN
SEQUENTIAL SYNTHESIS OF FUNCTIONALIZED ALKENES 597
9.5 SILYLATIVE COUPLING CYCLIZATION OF SILICON-CONTAINING DIENES 603
9.6 RING-CLOSING METATHESIS OF SILICON-CONTAINING DIENES 605
XII
CONTENTS
9.6.1 RING-CLOSING METATHESIS OF VINYLSILICON COMPOUNDS 606
9.6.2 RING-CLOSING METATHESIS OF ALLYLSILICON COMPOUNDS 609
9.6.3 RING-CLOSING METATHESIS OF ALKENYL-SUBSTITUTED SILAKETALS 612
9.6.4 ASYMMETRIC RING-CLOSING METATHESIS 616
9.7 ACYCLIC DIENE METATHESIS (ADMET) VERSUS SILYLATIVE COUPLING (SC)
POLYCONDENSATION OF SILICON-CONTAINING DIENES 617
9.8 RING-OPENING METATHESIS POLYMERIZATION OF SILYL-SUBSTITUTED
CYCLOALKENES 622
REFERENCES 626
10 RING-CLOSING METATHESIS IN THE LARGE-SCALE SYNTHESIS
OF PHARMACEUTICALS 633
VITTORIO FARINA ANDANDRAS HORVATH
10.1 INTRODUCTION 633
10.2 CILUPREVIR (BILN2061) AND ANALOGS 634
10.3 VANIPREVIR (MK-7009) 639
10.4 SIMEPREVIR (TMC435) 641
10.5 SB-462795 643
10.6 APPROACHES TO THE SCALE-UP OF RCM REACTIONS 646
10.6.1 CHOICE OF CATALYST 647
10.6.2 CHOICE OF SOLVENT 648
10.6.3 USE OF ADDITIVES 649
10.6.4 DETERMINING AND CONTROLLING SIDE REACTIONS 649
10.6.5 CONTROLLING THE INITIATION SITE 651
10.6.6 EFFECTIVE MOLARITY: HOW TO ACHIEVE PRACTICAL CONCENTRATIONS 653
10.6.7 EFFECT OF SOLVENT, REAGENT, AND SUBSTRATE IMPURITIES ON TON AND
TOF 655
10.6.8 EFFECT OF AIR AND MOISTURE 656
10.6.9 ISOLATION AND RUTHENIUM REMOVAL 656
REFERENCES 657
11 METATHESIS STRATEGIES IN DIVERSITY-ORIENTED SYNTHESIS 659
ALAN ROLFE AND LISA A. MARCAURELLE
11.1 INTRODUCTION 659
11.2 SYNTHESIS OF SMALL- TO MEDIUM-SIZED RINGS VIA METATHESIS
STRATEGIES 659
11.3 SYNTHESIS OF MACROCYCLES VIA METATHESIS STRATEGIES 670
11.4 METATHESIS CASCADE STRATEGIES IN DIVERSITY-ORIENTED SYNTHESIS 673
11.5 SYNTHESIS OF SMALL- TO MEDIUM-SIZED RINGS VIA METATHESIS CASCADE
STRATEGIES 674
11.6 SYNTHESIS OF MACROCYCLES VIA METATHESIS CASCADE STRATEGIES 681
11.7 METATHESIS STRATEGIES IN SOLID-PHASE LIBRARY SYNTHESIS 684
11.8 IMMOBILIZED SCAVENGERS AND CATALYSTS 692
CONTENTS
XIII
11.9 CONCLUSIONS 693
ACKNOWLEDGMENTS 695
REFERENCES 695
12 OLEFIN METATHESIS: COMMERCIAL APPLICATIONS AND FUTURE
OPPORTUNITIES 699
DIANA STOIANOVA, ADAM JOHNS, AND RICHARD PEDERSON
12.1 INTRODUCTION 699
12.2 RUTHENIUM OLEFIN METATHESIS CATALYSTS 700
12.3 RENEWABLE SEED OIL FEEDSTOCKS 702
12.3.1 BACKGROUND 702
12.3.2 VALUE-ADDED PRODUCTS FROM THE METATHESIS OF SEED OILS 703
12.4 PRODUCTION OF FATTY ACIDS AND AMINO ACIDS FROM RENEWABLES 706
12.4.1 A. TO-DIACIDS FROM RENEWABLES 706
12.4.2 A-AMINOACIDS FROM RENEWABLES 708
12.5 OLEFIN METATHESIS AND NATURAL MATERIALS CHEMISTRY 710
12.5.1 HYDROGENATED METATHESIZED SOYBEAN OIL (HMSBO) WAX 710
12.5.2 HIGHER MELTING POINT HMSBO COMPOSITIONS 711
12.5.3 TERPENES 711
12.5.4 NATURAL RUBBER 712
12.5.5 HYDROGENATED NITRILE-BUTADIENE RUBBER (HNBR) 714
12.6 PHARMACEUTICAL APPLICATIONS 715
12.6.1 HEPATITIS C PROTEASE INHIBITOR 715
12.6.2 STAPLED PEPTIDES 716
12.7 ROMP-DERIVED OLIGOMERS FOR FACILITATED SYNTHESIS 717
12.7.1 INTRODUCTION AND BACKGROUND 717
12.7.2 OLIGOMERIC MONOAMINE HYDROCHLORIDE (OMAM-HCL) 718
12.7.3 OLIGOMERIC BIS-ACID CHLORIDE (OBAC) 719
12.7.4 OLIGOMERIC TRIPHENYLPHOSPHINE (OTPP) 719
12.7.5 ETHYLENE FROM RENEWABLE FEEDSTOCKS 721
12.8 CONCLUSION 721
REFERENCES 722
INDEX 727
|
| any_adam_object | 1 |
| author2 | Grubbs, Robert H. 1942-2021 |
| author2_role | edt |
| author2_variant | r h g rh rhg |
| author_GND | (DE-588)124993532 |
| author_facet | Grubbs, Robert H. 1942-2021 |
| building | Verbundindex |
| bvnumber | BV042407321 |
| classification_rvk | VK 6000 |
| ctrlnum | (OCoLC)909801371 (DE-599)BVBBV042407321 |
| discipline | Chemie / Pharmazie |
| edition | 2. ed. |
| format | Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01656nam a2200397 cc4500</leader><controlfield tag="001">BV042407321</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">20151020 </controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">150313s2015 d||| |||| 00||| eng d</controlfield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">9783527339495</subfield><subfield code="c">print</subfield><subfield code="9">978-3-527-33949-5</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(OCoLC)909801371</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)BVBBV042407321</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-604</subfield><subfield code="b">ger</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1="0" ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="049" ind1=" " ind2=" "><subfield code="a">DE-11</subfield><subfield code="a">DE-703</subfield><subfield code="a">DE-29T</subfield><subfield code="a">DE-19</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">VK 6000</subfield><subfield code="0">(DE-625)147413:253</subfield><subfield code="2">rvk</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Handbook of metathesis</subfield><subfield code="n">2</subfield><subfield code="p">Applications in organic synthesis</subfield><subfield code="c">ed. by Robert H. Grubbs ...</subfield></datafield><datafield tag="250" ind1=" " ind2=" "><subfield code="a">2. ed.</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="a">Weinheim</subfield><subfield code="b">Wiley-VCH</subfield><subfield code="c">2015</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">XXVI, 743 S.</subfield><subfield code="b">graph. Darst.</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Organische Synthese</subfield><subfield code="0">(DE-588)4075695-6</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Metathese</subfield><subfield code="g">Chemie</subfield><subfield code="0">(DE-588)4169656-6</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="689" ind1="0" ind2="0"><subfield code="a">Metathese</subfield><subfield code="g">Chemie</subfield><subfield code="0">(DE-588)4169656-6</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="1"><subfield code="a">Organische Synthese</subfield><subfield code="0">(DE-588)4075695-6</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Grubbs, Robert H.</subfield><subfield code="d">1942-2021</subfield><subfield code="0">(DE-588)124993532</subfield><subfield code="4">edt</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="w">(DE-604)BV025307693</subfield><subfield code="g">2</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, EPUB</subfield><subfield code="z">978-3-527-69404-4</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, MOBI</subfield><subfield code="z">978-3-527-69403-7</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, PDF</subfield><subfield code="z">978-3-527-69402-0</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">DNB Datenaustausch</subfield><subfield code="q">application/pdf</subfield><subfield code="u">http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027842890&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="999" ind1=" " ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-027842890</subfield></datafield></record></collection> |
| id | DE-604.BV042407321 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T01:20:41Z |
| institution | BVB |
| isbn | 9783527339495 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027842890 |
| oclc_num | 909801371 |
| open_access_boolean | |
| owner | DE-11 DE-703 DE-29T DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-703 DE-29T DE-19 DE-BY-UBM |
| physical | XXVI, 743 S. graph. Darst. |
| publishDate | 2015 |
| publishDateSearch | 2015 |
| publishDateSort | 2015 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Handbook of metathesis 2 Applications in organic synthesis ed. by Robert H. Grubbs ... 2. ed. Weinheim Wiley-VCH 2015 XXVI, 743 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Synthese (DE-588)4075695-6 gnd rswk-swf Metathese Chemie (DE-588)4169656-6 gnd rswk-swf Metathese Chemie (DE-588)4169656-6 s Organische Synthese (DE-588)4075695-6 s DE-604 Grubbs, Robert H. 1942-2021 (DE-588)124993532 edt (DE-604)BV025307693 2 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-69404-4 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-69403-7 Erscheint auch als Online-Ausgabe, PDF 978-3-527-69402-0 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027842890&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Handbook of metathesis Organische Synthese (DE-588)4075695-6 gnd Metathese Chemie (DE-588)4169656-6 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4169656-6 |
| title | Handbook of metathesis |
| title_auth | Handbook of metathesis |
| title_exact_search | Handbook of metathesis |
| title_full | Handbook of metathesis 2 Applications in organic synthesis ed. by Robert H. Grubbs ... |
| title_fullStr | Handbook of metathesis 2 Applications in organic synthesis ed. by Robert H. Grubbs ... |
| title_full_unstemmed | Handbook of metathesis 2 Applications in organic synthesis ed. by Robert H. Grubbs ... |
| title_short | Handbook of metathesis |
| title_sort | handbook of metathesis applications in organic synthesis |
| topic | Organische Synthese (DE-588)4075695-6 gnd Metathese Chemie (DE-588)4169656-6 gnd |
| topic_facet | Organische Synthese Metathese Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027842890&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV025307693 |
| work_keys_str_mv | AT grubbsroberth handbookofmetathesis2 |