Cinchona alkaloids in synthesis and catalysis: ligands, immobilization and organocatalysis
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| Format: | Book |
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| Language: | English |
| Published: |
Weinheim
WILEY-VCH
2009
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Item Description: | Literaturangaben |
| Physical Description: | XX, 525 S. Ill., graph. Darst. 240 mm x 170 mm |
| ISBN: | 9783527324163 |
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Record in the Search Index
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VII CONTENTS PREFACE XV BIOGRAPHY XVII LIST OF CONTRIBUTORS XIX 1 AN
OVERVIEW OF CINCHONA ALKALOIDS IN CHEMISTRY I CHOONG EUI SONG 1.1 BRIEF
HISTORY 1 1.2 ACTIVE SITES IN CINCHONA ALKALOIDS AND THEIR DERIVATIVES 3
1.3 STRUCTURAL INFORMATION ON CINCHONA ALKALOIDS 4 1.4 HOW THIS BOOK IS
ORGANIZED 8 REFERENCES 9 PART ONE CINCHONA ALKALOID DERIVATIVES AS
CHIRALITY INDUCERS IN METAL-CATALYZED REACTIONS 11 2 CINCHONA ALKALOIDS
AS CHIRALITY TRANSMITTERS IN METAL-CATALYZED ASYMMETRIC REDUCTIONS 13
HANS-ULRICH BLASER 2.1 INTRODUCTION 3 2.2 HOMOGENEOUS SYSTEMS FOR
KETONE REDUCTIONS 14 2.3 HETEROGENEOUS PT AND PD CATALYSTS MODIFIED WITH
CINCHONA ALKALOIDS 25 2.3.1 BACKGROUND 15 2.3.2 CATALYSTS 16 2.3.3
MODIFIERS AND SOLVENTS 16 2.3.4 SUBSTRATE SCOPE FOR PT CATALYSTS 17
2.3.4.1 A-KETO ACID DERIVATIVES 17 2.3.4.2 A,Y-DIKETO ESTERS 18 2.3.4.3
FLUORINATED RETONES 38 2.3.4.4 OT-KETO ACETAIS 20 2.3.4. BIBLIOGRAFISCHE
INFORMATIONEN HTTP://D-NB.INFO/993261310 DIGITALISIERT DURCH VIM
CONTENTS 2.3.5 SUBSTRATE SCOPE FOR PD CATALYSTS 21 2.4 INDUSTRIAL
APPLICATIONS 22 2.5 CONCLUSIONS 25 REFERENCES 26 3 CINCHONA ALKALOIDS AS
CHIRAL LIGANDS IN ASYMMETRIC OXIDATIONS 29 DAVIDJ. AGER 3.1 INTRODUCTION
29 3.2 ASYMMETRIC DIHYDROXYLATION OF ALKENES 30 3.2.1 EARLY REACTIONS 30
3.2.2 BISALKALOID LIGANDS 33 3.2.3 MECHANISM 35 3.2.4 VARIATIONS 36
3.2.5 SUBSTRATES AND SELECTIVITY 38 3.2.5.1 SIMPLE ALKENES 38 3.2.5.2
FUNCTIONALIZED ALKENES 38 3.2.5.3 POLYENES 43 3.2.5.3.1 NONCONJUGATE
OLEFINS 43 3.2.5.3.2 CONJUGATED POLYENES 43 3.2.5.4 DOUBLE ASYMMETRIC
INDUCTION 44 3.2.5.5 RESOLUTIONS 50 3.2.6 SOME REACTIONS OF 1,2-DIOLS 51
3.2.6.1 CYCLIC SULFATES AND SULFITES 54 3.3 AMINOHYDROXYLATION 56 3.4
SULFUR OXIDATIONS 61 3.5 SUMMARY 61 CONTENTS IX 4.2.5.1 LEWIS ACID
ASSISTED NUCLEOPHILIC ADDITION OF KETENES (OR SULFENES) TO ALDEHYDES:
SS-LACTONE AND SS-SULTONE SYNTHESIS 86 4.2.5.2 LEWIS ACID ASSISTED
NUCLEOPHILIC ADDITION OF KETENES TO IMINES: SS-LACTAM SYNTHESIS 90
4.2.5.3 APPLICATIONS OF CHIRAL KETENE ENOLATES TO FORMAL [4 + 2] TYPE
CYCLIZATION 92 4.2.6 AZA-HENRY REACTION 92 4.2.7 ENANTIOSELECTIVE
HYDROPHOSPHONYLATION 93 4.3 MISCELLANEOUS REACTIONS 94 4.3.1 CLAISEN
REARRANGEMENTS 94 4.3.2 PD-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTIONS 95
4.3.3 PAUSON-KHAND REACTION 97 4.3.4 ASYMMETRIC DIMERIZATION OF
BUTADIENE 98 4.3.5 ENANTIOTOPIC DIFFERENTIATION REACTION OF MESOCYCLIC
ANHYDRIDES 98 4.4 CINCHONA-BASED CHIRAL LIGANDS IN C-F BOND FORMING
REACTIONS 99 4.5 CONCLUSIONS 100 REFERENCES 101 PART TWO CINCHONA
ALKALOID DERIVATIVES AS CHIRAL ORGANOCATALYSTS 105 5 CINCHONA-BASED
ORGANOCATALYSTS FOR ASYMMETRIC OXIDATIONS AND REDUCTIONS 107 UEON SANG
SHIN, JE EUN LEE, JUNG WOON YANG, AND CHOONG EUI SONG 5.1 INTRODUCTION
107 5.2 CINCHONA-BASED ORGANOCATALYSTS IN ASYMMETRIC OXIDATIONS 108 X
CONTENTS 6.2 ORGANOCATALYTIC NUCLEOPHILIC -SUBSTITUTION OF CARBONYL
DERIVATIVES 131 6.3 CINCHONA ALKALOIDS IN ASYMMETRIE ORGANOCATALYSIS 133
6.4 THE PIONEER WORKS FOR PHASE-TRANSFER CATALYTIC A-SUBSTITUTION 134
6.5 A-SUBSTITUTION OF A-AMINO ACID DERIVATIVES VIA PTC 135 6.5.1
MONOALKYLATION OF BENZOPHENONE IMINES OF GLYCINE ESTERS 135 6.5.2
ALKYLATION OF A-MONOSUBSTITUTED A-AMINO ACID DERIVATIVES 348 6.6
A-SUBSTITUTION OF OTHER CARBONYL DERIVATIVES VIA PTC 150 6.6.1
A-SUBSTITUTION OF MONOCARBONYL COMPOUNDS 150 6.6.2 A-SUBSTITUTION OF
SS-KETO CARBONYL COMPOUNDS 153 6.7 A-HETEROATOM SUBSTITUTION VIA PTC 156
6.7.1 A-HYDROXYLATION OF CARBONYL DERIVATIVES 356 6.7.2 A-FLUORINATION
OF CARBONYL DERIVATIVES 157 6.8 NUCLEOPHILIC A-SUBSTITUTION OF CARBONYL
DERIVATIVES VIA NON-PTC 157 6.8.1 A-ARYLATION OF CARBONYL DERIVATIVES
358 6.8.2 A-HYDROXYLATION OF CARBONYL DERIVATIVES 359 6.8.3
A-HALOGENATION OF CARBONYL DERIVATIVES 360 6.8.4 A-AMINATION OF CARBONYL
DERIVATIVES 262 6.8.5 A-SULFENYLATION OF CARBONYL DERIVATIVES 365 6.9
CONCLUSIONS 165 REFERENCES 366 7 CINCHONA-MEDIATED ENANTIOSELECTIVE
PROTONATIONS 171 CONTENTS XI 8.2.2 HENRY REACTIONS 206 8.3 MANNICH AND
NITRO-MANNICH REACTIONS 209 8.3.1 MANNICH REACTIONS 209 8.3.2
NITRO-MANNICH (AZA-HENRY) REACTIONS 215 8.4 ALDOL- AND MANNICH-RELATED
REACTIONS 218 8.4.1 DARZENS REACTIONS 218 8.4.2 MORITA-BAYLIS-HILLMAN
REACTIONS AND AZA-MORITA-BAYLIS-HILLMAN REACTIONS 221 8.4.2.1
MORITA-BAYLIS-HILLMAN REACTIONS 221 8.4.2.2 AZA-MORITA-BAYLIS-HILLMAN
REACTIONS 225 8.4.3 NUCLEOPHILIC ADDITION OF AMMONIUM RETENE ENOLATE TO
C=O OR C=N BONDS 228 8.5 CYANATION REACTIONS 229 8.5.1 CYANOHYDRIN
SYNTHESIS 229 8.5.2 STRECKER SYNTHESIS 232 8.6 TRIFLUOROMETHYLATION 234
8.7 FRIEDEL-CRAFTS TYPE ALKYLATION 237 8.8 HYDROPHOSPHONYLATION 240 8.9
CONCLUSIONS 244 REFERENCES 244 9 CINCHONA-CATALYZED NUCLEOPHILIC
CONJUGATE ADDITION TO ELECTRON-DEFICIENT C=C DOUBLE BONDS 249 JI WOONG
LEE, HYEONG BIN JANG, AND CHOONG EUI SONG 9.1 INTRODUCTION 249 XII
CONTENTS 10.3 ASYMMETRIC CYCLOADDITIONS CATALYZED BY BIFUNCTIONAL
CINCHONA ALKALOIDS 308 10.4 ASYMMETRIC CYCLOADDITION REACTIONS CATALYZED
BY CINCHONA-BASED PRIMARY AMINES 312 10.5 ASYMMETRIC CYCLOADDITION
CATALYZED BY CINCHONA-BASED PHASE-TRANSFER CATALYSTS 320 10.6 CONCLUSION
323 REFERENCES 323 11 CINCHONA-BASED ORGANOCATALYSTS FOR
DESYMMETRIZATION OF MESO-COMPOUNDS AND (DYNAMIC) KINETIC RESOLUTION OF
RACEMIC COMPOUNDS 325 JI WOONG LEE, HYEONG BIN JANG, JE EUN LEE, AND
CHOONG EUI SONG 11.1 INTRODUCTION 325 11.2 DESYMMETRIZATION OF
MESO-COMPOUNDS 326 11.2.1 DESYMMETRIZATION OF MESO-CYCLIC ANHYDRIDES 326
11.2.1.1 APPLICATIONS 336 11.2.2 DESYMMETRIZATION OF WESO-DIOLS 336
11.2.3 DESYMMETRIZATION OF MESO-ENDOPEROXIDES 341 11.2.4
DESYMMETRIZATION OF MESO-PHOSPHOLENES VIA ALKENE ISOMERIZATION 344
11.2.5 DESYMMETRIZATION OF MESO-EPOXY PHOSPHOLENES TO ALLYL ALCOHOLS VIA
REARRANGEMENT 345 11.2.6 DESYMMETRIZATION OF PROCHIRAL RETONES BY MEANS
OF HORNER-WADSWORTH-EMMONS REACTION 346 11.3 (DYNAMIC) RINETIC
RESOLUTION OF RACEMIC COMPOUNDS 346 CONTENTS XIII 12.4.1.1 THE ETHYNYL
GROUP IS ANYTHING BUT A SPECTATOR SUBSTITUENT 371 12.4.2 FLUORINATION OF
THE VINYL SIDE CHAIN 374 12.4.3 OXIDATION AND OXIDATIVE CLEAVAGE OF THE
VINYL GROUP 375 12.4.3.1 OXIDATIVE FUNCTIONALIZATION OF QUINCORINE AND
QUINCORIDINE 380 12.4.4 DEGRADATION OF THE VINYL SIDE CHAIN: SYNTHESIS
OF CINCHONA ALKALOID RETONES 381 12.5 SELECTED NOVEL TRANSFORMATIONS OF
THE QUINUCLIDINE MOIETY OF CINCHONA ALKALOIDS 382 12.5.1 CAGE HELICITY
AND FURTHER CONSEQUENCES: NUCLEOPHILIC ATTACK ON QUINUCLIDIN-3-ONES 382
12.5.2 TRANSFORMATIONS AT CARBON C6 AND FORMATION OF BRIDGEHEAD BICYCLIC
LACTAMS 389 12.5.3 FUNCTIONALIZATION OF OTHER QUINUCLIDINE CARBONS, FOR
EXAMPLE, C5 AND C7 393 12.6 NUCLEOPHILIC SUBSTITUTION AT CARBON C9 394
12.6.1 UNUSUAL STERIC COURSE OF SOLVOLYSIS OF C9-ACTIVATED ALKALOIDS:
ACCESS TO C9-EPI-CONFIGURED STEREOISOMERS 394 12.6.2 REPLACING THE
C9-HYDROXY GROUP BY ALTERNATIVE SUBSTITUENTS 396 12.6.3 TRANSFORMATIONS
OF QCI AND QCD AT CARBON C9: ACCESS TO A NOVEL CLASS OF SMALL MOLECULE
LIGANDS 399 12.7 NOVEL REARRANGEMENTS OF THE AZABICYCLIC MOIETY 403
12.7. XIV CONTENTS 13.3.5 OTHER CHROMATOGRAPHIE TECHNIQUES 452 13.4
CINCHONA ALKALOIDS AS CHIRAL SOLVATING (SHIFT) AGENTS IN NMR
SPECTROSCOPY 453 13.5 CINCHONA-BASED SENSORS, RECEPTORS, AND MATERIALS
FOR SEPARATION AND ANALYTICS 455 REFERENCES 464 APPENDIX: TABULAR SURVEY
OF SELECTED CINCHONA-PROMOTED ASYMMETRIC REACTIONS 471 JI WOONG LEE AND
CHOONG EUI SONG INDEX 507 |
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| indexdate | 2024-07-20T10:28:54Z |
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| isbn | 9783527324163 |
| language | English |
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| physical | XX, 525 S. Ill., graph. Darst. 240 mm x 170 mm |
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| spelling | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis ed. by Choong Eui Song Weinheim WILEY-VCH 2009 XX, 525 S. Ill., graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Literaturangaben Catalysis Chirality Cinchona alkaloids Organic compounds Synthesis Cinchonaalkaloide (DE-588)4466840-5 gnd rswk-swf Cinchonaalkaloide (DE-588)4466840-5 s DE-604 Song, Choong-Eui Sonstige (DE-588)112631150 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3261156&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=018929644&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis Catalysis Chirality Cinchona alkaloids Organic compounds Synthesis Cinchonaalkaloide (DE-588)4466840-5 gnd |
| subject_GND | (DE-588)4466840-5 |
| title | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis |
| title_auth | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis |
| title_exact_search | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis |
| title_full | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis ed. by Choong Eui Song |
| title_fullStr | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis ed. by Choong Eui Song |
| title_full_unstemmed | Cinchona alkaloids in synthesis and catalysis ligands, immobilization and organocatalysis ed. by Choong Eui Song |
| title_short | Cinchona alkaloids in synthesis and catalysis |
| title_sort | cinchona alkaloids in synthesis and catalysis ligands immobilization and organocatalysis |
| title_sub | ligands, immobilization and organocatalysis |
| topic | Catalysis Chirality Cinchona alkaloids Organic compounds Synthesis Cinchonaalkaloide (DE-588)4466840-5 gnd |
| topic_facet | Catalysis Chirality Cinchona alkaloids Organic compounds Synthesis Cinchonaalkaloide |
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