Asymmetric catalysis on industrial scale: challenges, approaches, and solutions
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| Format: | Buch |
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| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2010
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| Ausgabe: | 2. ed. |
| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Beschreibung: | XXXVII, 542 S. Ill., graph. Darst. |
| ISBN: | 9783527324897 |
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| 650 | 4 | |a Enantioselective catalysis |v Case studies | |
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CONTENTS LIST OF CONTRIBUTORS XIX INTRODUCTION XXIX HANS-ULRICH BLASER
AND HANS-JUERGEN FEDERSEI PART I NEW PROCESSES FOR EXISTING ACTIVE
COMPOUNDS (APIS) 1 1 SOME RECENT EXAMPLES IN DEVELOPING BIOCATALYTIC
PHARMACEUTICAL PROCESSES 3 JUNHUA TAO, J. LIU, AND Z. CHEN 1.1
INTRODUCTION 3 1.2 LEVETIRACETAM (KEPPRA) 3 1.3 ATORVASTATIN (LIPITOR)
6 1.4 PREGABALIN (LYRICA) 8 1.5 CONCLUSION 11 ACKNOWLEDGMENTS 11
REFERENCES 11 2 ENANTIOSELECTIVE HYDROGENATION: APPLICATIONS IN PROCESS
R&D OF PHARMACEUTICALS 13 KURT PIINTENER AND MICHELANGELO SCALONE 2.1
INTRODUCTION 13 2.2 CARBONYL HYDROGENATIONS 13 2.2.1 ASYMMETRIC
HYDROGENATION WITH DYNAMIC KINETIC RESOLUTION OF RACEMIC
L,4-DIBENZYLPIPERIDIN-3-ONE 13 2.2.2 ASYMMETRIC HYDROGENATION OF METHYL
3-OXOTETRADECANOATE 16 2.2.3 ASYMMETRIC HYDROGENATION OF
1,1,1-TRIFLUOROACETONE 17 2.2A ASYMMETRIC TRANSFER HYDROGENATION OF
LEVODIONE 19 2.3 INLINE HYDROGENATION 21 BIBLIOGRAFISCHE INFORMATIONEN
HTTP://D-NB.INFO/997573457 DIGITALISIERT DURCH VI CONTENTS 3 CHIRAL
LACTONES BY ASYMMETRIC HYDROGENATION - A STEP FORWARD IN (+)-BIOTIN
PRODUCTION 27 WERNER BONRATH, REINHARD KARGE, THOMAS NETSCHER, FELIX
ROESSLER, AND FELIX SPINDLER 3.1 INTRODUCTION: (+)-BIOTIN AS AN EXAMPLE
FOR THE INDUSTRIAL PRODUCTION OF VITAMINS 27 3.2 COMMERCIAL SYNTHESES
AND OTHER ROUTES TO (+)-BIOTIN BY TOTAL SYNTHESIS 28 3.3 CATALYTIC
ASYMMETRIC REDUCTION OF CYCLIC ANHYDRIDE TO D-LACTONE 31 3.4 CONCLUSION
37 ACKNOWLEDGMENTS 38 REFERENCES 38 4 BIOCATALYTIC ASYMMETRIC OXIDATION
FOR THE PRODUCTION OF BICYCLIC PROLINE PEPTIDOMIMETICS 41 JAMES J.
LALONDE AND JACK LIANG 4.1 INTRODUCTION 41 4.2 DEVELOPMENT OF ROUTES TO
1 AND 2 43 4.2.1 EARLY ROUTES TO 1 43 4.2.1.1 SYNTHESIS OF CYCLIC AMINO
ACIDS VIA CYANATION OF IMINES 45 4.2.2 EARLY ROUTES TO 2 46 4.3
ASYMMETRIC BIOCATALYTIC AMINE OXIDATION 48 4.4 ENZYME EVOLUTION -
CURRENT STATE OF THE ART 50 4.5 AMINE OXIDASE EVOLUTION 53 4. CONTENTS
VII 5.6 ASYMMETRIC REDUCTION OF KETONES BEARING THE
3,6,7,8-TETRAHYDROCHROMENO[7,8-D]IMIDAZOLE SKELETON 70 5.7 LARGE-SCALE
ASYMMETRIC SYNTHESIS OF THE 3,6,7,8-TETRAHYDROCHROMENO[7,8-D]IMIDAZOLE
BYK 405879 71 5.8 CONCLUSIONS 75 ACKNOWLEDGMENTS 76 REFERENCES 76 PARTII
PROCESSES FOR IMPORTANT BUILDINGS BLOCKS 79 6 APPLICATION OF A
MULTIPLE-ENZYME SYSTEM FOR CHIRAL ALCOHOL PRODUCTION 81 JUNZO HASEGAWA,
HIROKAZU NANBA, AND YOSHIHIKO YASOHARA 6.1 INTRODUCTION 81 6.2
CONSTRUCTION OF AN ENZYMATIC REDUCTION SYSTEM 82 6.2.1 SEARCHING THE
CARBONYL REDUCTASES FOR MAKING THE LIBRARY 83 6.2.1.1 REDUCTASES FOR
CHIRAL HYDROXYCARBOXYLIC ACID ESTER PRODUCTION 83 6.2.1.2 COOPERATION OF
REDUCTASE SI AND GLUCOSE DEHYDROGENASE 84 6.2.1.3 REDUCTASE FOR CHIRAL
HALOHYDRIN PRODUCTION 88 6.2.1.4 REDUCTASES FOR CHIRAL 3-PYRROLIDINOL
PRODUCTION 89 6.2.1.5 REDUCTASE FOR CHIRAL PYRIDYLETHANOL DERIVATIVE
PRODUCTION 92 6.2.2 SEARCHING FOR A TOUGH FDH AGAINST HALO KETONES 95
VIII CONTENTS 7 A CONCLUSION 125 ACKNOWLEDGMENTS 125 REFERENCES 126 8
ASYMMETRIC HYDROGENATION OF A 2-LSOPROPYLCINNAMIC ACID DERIVATIVE EN
ROUTE TO THE BLOOD PRESSURE-LOWERING AGENT ALISKIREN 127 JEROEN A. F.
BOOGERS, DIRK SARTOR, ULJRIED FELFER, MARTINA KOTTHAUS, GERHARD
STEINBAUER, BERT DIELEMANS, LAURENT LEFORT, ANDRE H. M. DE VUES, AND
JOHANNES G. DE VRIES 8.1 INTRODUCTION 127 8.2 DEVELOPMENT OF MONODENTATE
PHOSPHORAMIDITES AS LIGANDS FOR ASYMMETRIC HYDROGENATION 127 8.3 INSTANT
LIGAND LIBRARIES OF MONODENTATE BINOL-BASED PHOSPHORAMIDITES 130 8.4
ALISKIREN* 132 8.5 HIGH-THROUGHPUT SCREENING IN SEARCH OF A CHEAP
PHOSPHORAMIDITE LIGAND 134 8.6 MIXTURES OF LIGANDS 135 8.7 FURTHER
SCREENING OF CONDITIONS 138 8.8 VALIDATION AND PILOT PLANT RUN 138 8.9
INSTANT LIGAND LIBRARY SCREENING TO FURTHER OPTIMIZE RATE AND EE 141
8.10 VALIDATIONS 143 8.11 RECENT DEVELOPMENTS IN THE ASYMMETRIC
HYDROGENATION OF 3 144 CONTENTS \ IX 9.4.1 ETHYL (S)-AUYLGLYCINATE
P-TOLUENESULFONIC ACID SALT 360 9.4.2 (R)-A-METHYL-4-FLUOROPHENYLALANINE
163 9.4.3 A»II-(2J?,3I2)- / 6-METHYL-4-FLUOROPHENYLALANINE 164 9.5
CONCLUSION 367 REFERENCES 167 10 DEVELOPMENT OF EFFICIENT TECHNICAL
PROCESSES FOR THE PRODUCTION OF ENANTIOPURE AMINO ALCOHOLS IN THE
PHARMACEUTICAL INDUSTRY 373 FRANZ DIETRICH KLINGLER 10.1 INTRODUCTION
171 10.2 PHENYLEPHRINE 373 10.2.1 IN RETROSPECT: HISTORIC DEVELOPMENTS
AND THE CLASSICAL TECHNICAL SYNTHESIS 373 10.2.2 DEVELOPMENT OF A NEW
ASYMMETRIC SYNTHESIS FOR PHENYLEPHRINE 372 10.2.2.1 LIGAND AND METAL
SCREENING 375 10.2.2.2 OPTIMIZATION OF THE LIGAND 376 10.2.2.3
MECHANISTIC CONSIDERATIONS 376 10.2.2.4 OPTIMIZATION OF THE REACTION
CONDITIONS 377 10.2.2.5 WORKUP AND FINAL STEP TO PHENYLEPHRINE
HYDROCHLORIDE 178 10.3 ADRENALINE (EPINEPHRINE) 178 10.3.1 HISTORY AND
CLASSICAL SYNTHETIC ROUTE 378 10.3.2 DEVELOPMENT OF A NEW TECHNICAL
SYNTHESIS BASED ON ASYMMETRIC HYDROGENATION 180 10.4 LOBELINE 180 10.4.1
HISTORY AND DESCRIPTION OF THE CLASSICAL SYNTHESIS 380 10.4.2
DEVELOPMENT OF AN EFFICIENT TWO-STEP SYNTHESIS OF LOBELINE 182 X I
CONTENTS ACKNOWLEDGMENTS 204 REFERENCES 204 12 ELIMINATING BARRIERS IN
LARGE-SCALE ASYMMETRIC SYNTHESIS 207 HIDEO SHIMIZU, NOBORU SAYO, AND
TAKAO SAITO 12.1 INTRODUCTION 207 12.2 IMPROVEMENT OF THE SYNTHETIC
ROUTE TO BIARYL LIGANDS 208 12.3 DEVELOPMENT OF AN EFFICIENT PROCESS EN
ROUTE TO UNPROTECTED SS -AMINO ACIDS 234 12.4 CONCLUSION 237 REFERENCES
2J7 13 CATALYTIC ASYMMETRIC RING OPENING: A TRANSFER FROM ACADEMIA TO
INDUSTRY 219 DIRK SPIELVOGEL 13.1 INTRODUCTION 219 13.2 CATALYST
PREPARATION AND INITIAL OPTIMIZATION 223 13.3 FURTHER OPTIMIZATION 222
13 A PROCESS ADAPTATION 224 13.5 PROTECTING GROUP ADAPTATION 225 13.6
USE OF BENZOATEAS O-NUCLEOPHILE 226 13.7 CHEMICAL ELABORATION 227 13.8
CONCLUSION 227 ACKNOWLEDGMENTS 228 REFERENCES 229 14 ASYMMETRIC
BAEYER-VILLIGER REACTIONS USING WHOLE-CELL BIOCATALYSTS 233 ROLAND
CONTENTS XI 15 LARGE-SCALE APPLICATIONS OF HYDROLASES IN BIOCATALYTIC
ASYMMETRIC SYNTHESIS 249 ROLAND WOHLGEMUTH 15.1 INTRODUCTION 249 15.2
CHEMISTRY 253 15.3 BIOCATALYST 253 15.4 PROCESS SCREENING AND DESIGN 255
15.5 DOWNSTREAM PROCESSING AND PURIFICATION 257 15.6 FUTURE PROCESS
DEVELOPMENTS 259 15.7 PERSPECTIVES 259 REFERENCES 260 16 SCALE-UP
STUDIES IN ASYMMETRIC TRANSFER HYDROGENATION 265 A. JOHN BLACKER AND
PETER THOMPSON 16.1 BACKGROUND 265 16.2 REACTION COMPONENTS 267 16.2.1
THE CATALYST 267 16.2.2 THE HYDROGEN DONOR 272 16.2.3 THE SOLVENT 274
16.2.4 THE SUBSTRATE 274 16.2.5 THE PROCESS 277 16.3 CASE STUDIES 278
16.3.1 DILTIAZEM 278 16.3.2
(J?)-N-METHYL-A-METHYL-3',5'-BIS(TRIFLUOROMETHYL)BENZYLAMINE 280 16.3.3
DULOXETINE 282 16.3.4 (R)-STYRENE OXIDE 284 16.3.5
(S)-2-(3-NITROPHENYL)ETHYLAMINE HYDROCHLORIDE 285 XII I CONTENTS
ACKNOWLEDGMENTS 298 REFERENCES 298 18 THE POWER OF WHOLE-CELL REACTION:
EFFICIENT PRODUCTION OF HYDROXYPROLINE, SUGAR NUCLEOTIDES,
OLIGOSACCHARIDES, AND DIPEPTIDES 301 SHIN-ICHI HASHIMOTO, SATOSHI
KOIZUMI, AND AKIO OZAKI 18.1 INTRODUCTION 303 18.2 PRODUCTION OF
HYDROXYPROLINE BY ASYMMETRIC HYDROXYLATION OF L-PROLINE 302 18.2.1
SCREENING OF REGIO- AND STEREOSPECIFIC L-PROLINE HYDROXYLASES 303 18.2.2
CLONING AND CHARACTERIZATION OF PROLINE HYDROXYLASES 304 18.2.3
ENZYMATIC PRODUCTION OF HYDROXYPROLINE FROM L-PROLINE 304 18.2.4
PRODUCTION OF HYDROXYPROLINE FROM GLUCOSE 305 18.2.5 COMMERCIAL
PRODUCTION OF HYDROXYPROLINE 306 18.3 OLIGOSACCHARIDE PRODUCTION BY
BACTERIAL COUPLING 307 18.3.1 BACTERIAL GLYCOSYLTRANSFERASES 307 18.3.2
OLIGOSACCHARIDE SYNTHESIS WITH PURIFIED ENZYME PREPARATIONS 307 18.3.3
PRODUCTION OF SUGAR NUCLEOTIDES BY BACTERIAL COUPLING 308 18.3.4
PRODUCTION OF OLIGOSACCHARIDES BY BACTERIAL COUPLING 309 18.3.5
LARGE-SCALE PRODUCTION OF SUGAR NUCLEOTIDES AND OLIGOSACCHARIDE CONTENTS
XIII PART III PROCESSES FOR NEW CHEMICAL ENTITIES (NCES) 331 20 ENABLING
ASYMMETRIC HYDROGENATION FOR THE DESIGN OF EFFICIENT SYNTHESIS OF DRUG
SUBSTANCES 333 YONGKUI SUN, SHANE KRSKA, SCOTT SHULTZ, AND DAVID M.
TELLERS 20.1 INTRODUCTION 333 20.2 LAROPIPRANT 339 20.2.1 REACTION
DISCOVERY 339 20.2.2 REACTION OPTIMIZATION AND DEMONSTRATION 341
20.2.2.1 CATALYST IDENTIFICATION 341 20.2.2.2 SUBSTRATE SOLUBILITY 342
20.2.2.3 TEMPERATURE AND PRESSURE 342 20.2.2.4 CATALYST LOADING 343
20.2.2.5 REACTION STRESS TESTING 343 20.2.3 KILOGRAM-SCALE DEMONSTRATION
AND PILOT PLANT EXECUTION 344 20.2.4 PILOT PLANT IMPLEMENTATION 344
20.2.5 FINAL REMARKS 345 20.3 TARANABANT 345 20.3.1 DEVELOPMENT OF A
REDUCTIVE DYNAMIC KINETIC RESOLUTION APPROACH TOWARDS TARANABANT 347
20.3.2 DEVELOPMENT OF LONG-TERM ASYMMETRIC SYNTHESIS OF TARANABANT
UTILIZING ASYMMETRIC ENAMIDE HYDROGENATION 350 20. XIV CONTENTS 21.4.2.4
ISOLATION 387 21.5 SCALABLE ENZYMATIC MONOHYDROLYSIS OF THE DIESTER
(R,R)-1 388 21.5.1 RESIDUAL HEPTANE CONTENT 388 21.5.2 ISOLATION 389
21.6 PRODUCTION - EXPERIMENTAL PART 389 21.6.1 EQUIPMENT 389 21.6.2
RESOLUTION OF N-BOC-DIESTER-1 390 21.6.3 ISOLATION OF DIESTER (R,R)-1
390 21.6.4 MONOHYDROLYSIS OF DIESTER (R,R)-1 391 21.6.5 ISOLATION OF
MONOACID (R, R)-2 391 21.6.6 POINTS TO CONSIDER FOR FUTURE CAMPAIGNS 392
21.7 EVALUATION OF AN ENZYMATIC ALTERNATIVE - THE N-DIFLUOROETHYL
APPROACH 392 21.7.1 RESOLUTION OF DIESTER TRANS-RAC-1 393 21.7.2
MONOHYDROLYSIS OF DIESTER (R,R)-3 393 21.8 DISCUSSION 394
ACKNOWLEDGMENTS 395 REFERENCES 396 22 AN EFFICIENT, ASYMMETRIC SYNTHESIS
OF ODANACATIB, A SELECTIVE INHIBITOR OF CATHEPSIN K FOR THE TREATMENT OF
OSTEOPOROSIS, USING AN ENZYME-MEDIATED DYNAMIC KINETIC RESOLUTION 397
MATTHEW D. TRUPPO 22. CONTENTS | XV 23 BIOCATALYTIC ROUTES TO THE
CPIIB/LLLA ANTAGONIST LOTRAFIBAN, SB 214857 435 ANDY WELLS 23.1
INTRODUCTION 435 23.2 THE MEDICINAL CHEMISTRY ROUTE OF SYNTHESIS 416
23.3 THE FIRST BIOCATALYTIC ROUTE - A LATE-STAGE RESOLUTION 417 23.3.1
SYNTHESIS OF RACEMIC 1,4-BENZODIAZEPINES 438 23.3.2 FUNCTIONALIZATION AT
C-7-HALOGENATION AND AMINOCARBONYLATION 418 23.3.3 SCREENING FOR A
SUITABLE BIOCATALYST 422 23.3 A PRODUCT ISOLATION 424 23.3.5
BIORESOLUTION ON SCALE 425 23.4 EARLY-STAGE RESOLUTION 426 23.4.1
SUBSTRATE AND BIOCATALYST SELECTION 426 23.4.2 WORK-UP AND "IN SITU"
IODINATION 428 23.4.3 EARLY-STAGE RESOLUTION ON SCALE 429 23.4.4
RACEMIZATION OF (R)-1,4-BENZODIAZEPINES 429 23.4.5 THE 4,4'-BIPIPERIDINE
ISSUE SOLVED 430 23.4.6 CARBONYLATION USING 4,4'-BIPIPERIDINE 433 23.4.7
AMINOCARBONYLATION OF SB 240093 431 23.5 CATALASE FOR THE REMOVAL OF
IODIDE 432 23.5.1 THE FINAL STEPS 434 23.6 OTHER SYNTHETIC STRATEGIES TO
CHIRAL LOTRAFIBAN INTERMEDIATES 434 XVI CONTENTS 25.2 BACKGROUND AND
INTRODUCTION TO ZD7944 457 25.3 INTRODUCTION TO THE ZD7944 CBZ SULFOXIDE
STAGE 459 25 A PROCESS DEVELOPMENT OF ZD7944 CBZ SULFOXIDE 463 25.5
ADDITIONAL INVESTIGATIONS IN THE DEVELOPMENT OF ZD7944 CBZ SULFOXIDE 463
25.6 THE IMPACT OF OTHER STAGES ON THE ZD7944 CBZ SULFOXIDE PROCESS 464
25.7 SUMMARY OF ZD7944 465 25.8 BACKGROUND AND INTRODUCTION TO ZD2249
466 25.9 PROCESS DEVELOPMENT OFZD2249 CBZ SULFOXIDE 467 25.10 SUMMARY OF
ZD2249 469 25.11 COMPARISONS AND CONCLUSIONS 469 ACKNOWLEDGMENTS 470
REFERENCES 470 26 LARGE-SCALE APPLICATION OF ASYMMETRIC PHASE-TRANSFER
CATALYSIS FOR AMINO ACID SYNTHESIS 473 DANIEL E. PATTERSON, SHIPINGXIE,
LYNDA JONES, MARTIN H. OSTERHOUT, CHRISTOPHER G. HENRY, AND THOMAS D.
ROPER 26.1 INTRODUCTION 473 26.2 INITIAL STRATEGY 474 26.3 SYNTHESIS OF
4,4'-DIFLUOROBENZYLHYDRYL BROMIDE 475 26.4 INITIAL STUDIES AND
OPTIMIZATION 476 26.5 SCALE-UP OF THE PTC ALKYLATION 478 26. CONTENTS
XVII 27.4.4 IMPURITY ISSUES, ROBINSON ANNULATION, AND EE UPGRADE 492
27.4.4.1 EXPERIMENTAL DETAILS FOR CATALYTIC ASYMMETRIC PHASE-TRANSFER
ADDITION: PREPARATION OF (9AS)-8-CHLORO-7-METHOXY-9A-(2-PHENOXYETHYL)-
L,2,9,9A-TETRAHYDRO-3H-FLUOREN-3-ONE (9) 493 27.5 ETHER CLEAVAGE,
CYCLIZATION, AND CHLORINATION 494 27.6 CONCLUSION 495 ACKNOWLEDGMENTS
496 REFERENCES 496 28 ASYMMETRIC SYNTHESIS OF HCV AND HPV DRUG
CANDIDATES ON SCALE: THE CHOICE BETWEEN ENANTIOSELECTIVE AND
DIASTEREOSELECTIVE SYNTHESES 499 JEREMY D. COBB, BOB E. COOLEY, ROY C.
FLANAGAN, MARY M. JACKSON, LYNDA A. JONES, RICHARD T. MATSUOKA, ALAN
MILLAR, DANIEL E. PATTERSON, MATTHEW J. SHARP, JENNIFER F. TOCZKO,
SHIPING XIE, AND XIAOMING ZHOU 28.1 INTRODUCTION 499 28.2 GSK260983A (1)
FOR THE HPV 500 28.2.1 TARGET AND BACKGROUND 500 28.2.2 SYNTHETIC
STRATEGY 500 28.2.3 RACEMIC SYNTHESIS 501 28.2.4 ENANTIOSELECTIVE
SYNTHESIS THROUGH CHIRAL CATALYSIS 502 28.2.5 DIASTEREOSELECTIVE
SYNTHESIS THROUGH CHIRAL AUXILIARIES 503 XVIII CONTENTS 28.4 CONCLUSION
520 ACKNOWLEDGMENTS 521 REFERENCES 523 INDEX 523 |
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| genre | (DE-588)4522595-3 Fallstudiensammlung gnd-content |
| genre_facet | Fallstudiensammlung |
| id | DE-604.BV036118598 |
| illustrated | Illustrated |
| indexdate | 2024-07-20T10:33:11Z |
| institution | BVB |
| isbn | 9783527324897 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-019008636 |
| oclc_num | 696321965 |
| open_access_boolean | |
| owner | DE-29T DE-11 DE-83 DE-91S DE-BY-TUM DE-91G DE-BY-TUM DE-703 DE-384 |
| owner_facet | DE-29T DE-11 DE-83 DE-91S DE-BY-TUM DE-91G DE-BY-TUM DE-703 DE-384 |
| physical | XXXVII, 542 S. Ill., graph. Darst. |
| publishDate | 2010 |
| publishDateSearch | 2010 |
| publishDateSort | 2010 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Asymmetric catalysis on industrial scale challenges, approaches, and solutions ed. by Hans-Ulrich Blaser ... 2. ed. Weinheim Wiley-VCH 2010 XXXVII, 542 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Enantioselective catalysis Enantioselective catalysis Case studies Enantioselective catalysis Industrial applications Enantioselective catalysis Industrial applications Case studies Katalyse (DE-588)4029921-1 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Prozessentwicklung Technik (DE-588)4278925-4 gnd rswk-swf Maßstabübertragung (DE-588)4279219-8 gnd rswk-swf Chemische Verfahrenstechnik (DE-588)4069941-9 gnd rswk-swf (DE-588)4522595-3 Fallstudiensammlung gnd-content Asymmetrische Synthese (DE-588)4135603-2 s Katalyse (DE-588)4029921-1 s Maßstabübertragung (DE-588)4279219-8 s Chemische Verfahrenstechnik (DE-588)4069941-9 s Prozessentwicklung Technik (DE-588)4278925-4 s DE-604 Blaser, Hans-Ulrich Sonstige (DE-588)126075468 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3367557&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=019008636&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Asymmetric catalysis on industrial scale challenges, approaches, and solutions Enantioselective catalysis Enantioselective catalysis Case studies Enantioselective catalysis Industrial applications Enantioselective catalysis Industrial applications Case studies Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Prozessentwicklung Technik (DE-588)4278925-4 gnd Maßstabübertragung (DE-588)4279219-8 gnd Chemische Verfahrenstechnik (DE-588)4069941-9 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4135603-2 (DE-588)4278925-4 (DE-588)4279219-8 (DE-588)4069941-9 (DE-588)4522595-3 |
| title | Asymmetric catalysis on industrial scale challenges, approaches, and solutions |
| title_auth | Asymmetric catalysis on industrial scale challenges, approaches, and solutions |
| title_exact_search | Asymmetric catalysis on industrial scale challenges, approaches, and solutions |
| title_full | Asymmetric catalysis on industrial scale challenges, approaches, and solutions ed. by Hans-Ulrich Blaser ... |
| title_fullStr | Asymmetric catalysis on industrial scale challenges, approaches, and solutions ed. by Hans-Ulrich Blaser ... |
| title_full_unstemmed | Asymmetric catalysis on industrial scale challenges, approaches, and solutions ed. by Hans-Ulrich Blaser ... |
| title_short | Asymmetric catalysis on industrial scale |
| title_sort | asymmetric catalysis on industrial scale challenges approaches and solutions |
| title_sub | challenges, approaches, and solutions |
| topic | Enantioselective catalysis Enantioselective catalysis Case studies Enantioselective catalysis Industrial applications Enantioselective catalysis Industrial applications Case studies Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Prozessentwicklung Technik (DE-588)4278925-4 gnd Maßstabübertragung (DE-588)4279219-8 gnd Chemische Verfahrenstechnik (DE-588)4069941-9 gnd |
| topic_facet | Enantioselective catalysis Enantioselective catalysis Case studies Enantioselective catalysis Industrial applications Enantioselective catalysis Industrial applications Case studies Katalyse Asymmetrische Synthese Prozessentwicklung Technik Maßstabübertragung Chemische Verfahrenstechnik Fallstudiensammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3367557&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=019008636&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT blaserhansulrich asymmetriccatalysisonindustrialscalechallengesapproachesandsolutions |