Chiral amine synthesis: methods, developments and applications
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2010
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XXV, 494 S. Ill., graph. Darst. |
| ISBN: | 9783527325092 |
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Record in the Search Index
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IX CONTENTS FOREWORD VII PREFACE XVII LIST OF CONTRIBUTORS XXIII 1
STEREOSELECTIVE SYNTHESIS OF A-BRANCHED AMINES BY NUCLEOPHILIC ADDITION
OF UNSTABILIZED CARBANIONS TO IMINES 1 ANDRE B. CHARETTE 1.1
INTRODUCTION 1 1.2 OVERVIEW OF THE METHODS FOR THE PREPARATION OF IMINES
3 1.2.1 N-ARYL AND N-ALKYL IMINES AND HYDRAZONES 3 1.2.2 N-SULFINYL
IMINES 3 1.2.3 N-SULFONYL IMINES 4 1.2.4 N-PHOSPHINOYL IMINES 5 1.2.5
N-ACYL AND N-CARBAMOYL IMINES 6 1.3 CHIRAL AUXILIARY-BASED APPROACHES 6
1.3.1 IMINES DERIVED FROM CHIRAL ALDEHYDES 7 1.3.2 IMINES BEARING A
CHIRAL PROTECTING/ACTIVATING GROUP 9 1.4 CATALYTIC ASYMMETRIC
NUCLEOPHILIC ADDITION TO ACHIRAL IMINES 15 1.4.1 CATALYTIC ASYMMETRIC
ADDITION OF SP 3 HYBRIDIZED CARBANIONS 16 1.4.1.1 COPPER-CATALYZED
DIALKYLZINC ADDITIONS 16 1.4.1.2 ZINC ALKOXIDE-CATALYZED DIALKYLZINC
ADDITIONS 20 1.4.1.3 EARLY TRANSITION METAL (ZR, HF)-CATALYZED
DIALKYLZINC ADDITIONS 20 1.4.1.4 RHODIUM-CATALYZED DIALKYLZINC ADDITION
REACTIONS 23 1.4.2 CATALYTIC ASYMMETRIC ALLYLATION OF IMINES 24
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/99624493X DIGITALISIERT
DURCH X CONTENTS 1.5 CONCLUSION 42 REFERENCES 44 2 ASYMMETRIC METHODS
FOR RADICAL ADDITION TO IMINO COMPOUNDS 51 GREGORY K. FRIESTAD 2.1
BACKGROUND AND INTRODUCTION 51 2.2 INTERMOLECULAR RADICAL ADDITION
CHIRAL N-ACYLHYDRAZONES 52 2.2.1 DESIGN OF CHIRAL N-ACYLHYDRAZONES 52
2.2.2 PREPARATION OF CHIRAL N-ACYLHYDRAZONES 54 2.2.3 TIN-MEDIATED
ADDITION OF SECONDARY AND TERTIARY RADICALS 55 2.2.4 TIN-FREE RADICAL
ADDITION 58 2.2.5 MANGANESE-MEDIATED RADICAL ADDITION 59 2.2.6
MANGANESE-MEDIATED COUPLING WITH MULTIFUNCTIONAL PRECURSORS 60 2.2.6.1
HYBRID RADICAL-IONIC ANNULATION 60 2.2.6.2 PRECURSORS CONTAINING
HYDROXYL OR PROTECTED HYDROXYL GROUPS 62 2.2.6.3 ESTER-CONTAINING
N-ACYLHYDRAZONES 64 2.2.6.4 ADDITIONS TO KETONE HYDRAZONES 65 2.3
ASYMMETRIC CATALYSIS OF RADICAL ADDITION 67 2.4 CLOSING REMARKS 68
REFERENCES 69 3 ENANTIOSELECTIVE SYNTHESIS OF AMINES BY CHIRAL BRANSTED
ACID CATALYSTS 75 MASAHIRO TERADA AND NONE MOMIYAMA 3. CONTENTS XI
3.2.4.4 1,3-DIPOLAR CYDOADDITION REACTION 97 3.2.5 AZA-ENE-TYPE
REACTIONS 99 3.2.5.1 AZA-ENE-TYPE REACTION OF ALDIMINES WITH
ENECARBAMATES 99 3.2.5.2 CASCADE TRANSFORMATIONS BASED ON TANDEM
AZA-ENE-TYPE REACTION 99 3.2.5.3 TWO-CARBON HOMOLOGATION OF HEMIAMINAL
ETHERS 100 3.2.5.4 HOMOCOUPLING REACTION OF ENECARBAMATES 102 3.2.6
MISCELLANEOUS REACTIONS 104 3.2.6.1 AZA-COPE REARRANGEMENT 104 3.2.6.2
ALDOL-TYPE REACTION OF AZLACTONES WITH VINYL ETHERS 104 3.2.6.3
COOPERATIVE CATALYSIS BY METAL COMPLEXES AND CHIRAL PHOSPHORIC ADDS 106
3.3 CARBON-HYDROGEN BOND FORMING REACTIONS 108 3.3.1 TRANSFER
HYDROGENATION OF ACYDIC AND CYDIC IMINES 109 3.3.2 CASCADE TRANSFER
HYDROGENATION OF QUINOLINE AND PYRIDINE DERIVATIVES 113 3.3.3
APPLICATION OF TRANSFER HYDROGENATION TO CASCADE REACTION 116 3.4
CARBON*HETEROATOM BOND FORMING REACTIONS 117 3.4.1 HYDROPHOSPHONYLATION
(KABACHNIK-FIELDS REACTION) 117 3.4.2 FORMATION OF (HEMI)AMINALS 119
3.4.3 NUDEOPHILIC RING OPENING OF AZIRIDINES AND RELATED REACTIONS 121
XII CONTENTS 5.4 MISCELLANEOUS 174 5.5 CONDUSION 175 REFERENCES 176 6
CHIRAL AMINES FROM TRANSITION-METAL-MEDIATED HYDROGENATION AND TRANSFER
HYDROGENATION 179 TAMARA L CHURCH AND PHER C. ANDERSSON 6.1 SCOPE AND
RELATED PUBLICATIONS 179 6.2 CHIRAL AMINES WITH A DISUBSTITUTED NITROGEN
ATOM, HNR*R 1 179 6.2.1 DIRECT ASYMMETRIC HYDROGENATION OF ALKYL- AND
ARYL-SUBSTITUTED IMINES 1 79 6.2.1.1 DEVELOPMENT 180 6.2.1.1.1 A
REPRESENTATIVE SYNTHESIS 183 6.2.1.2 PRESSURE IN THE ASYMMETRIC
HYDROGENATION OF ALKYL- AND ARYL-SUBSTITUTED IMINES 183 6.2.1.3 REDUCING
THE ENVIRONMENTAL IMPACT OF THE REACTION 185 6.2.2 DIRECT ASYMMETRIC
HYDROGENATION OF HETEROAROMATICS 190 6.2.2.1 QUINOLINES AND
ISOQUINOLINES 190 6.2.2.1.1 QUINOLINES - A REPRESENTATIVE SYNTHESIS 195
6.2.2.1.2 ISOQUINOLINES - A REPRESENTATIVE SYNTHESIS 196 6.2.2.2
QUINOXALINES 197 6.2.2.3 PYRIDINES 198 6.2.3 DIRECT ASYMMETRIC
HYDROGENATION OF "ACTIVATED" IMINES 202 CONTENTS XIII 7.5 CONDUSIONS 243
REFERENCES 244 8 ENANTIOSELECTIVE HYDROGENATION OF ENAMINES WITH
MONODENTATE PHOSPHORUS LIGANDS 247 QIN-LIN ZHOU ANDJIAN-HUA XIE 8.1
INTRODUCTION 247 8.2 ASYMMETRIE HYDROGENATION OF ENAMIDES 249 8.2.1
CHIRAL MONODENTATE PHOSPHORAMIDITE LIGANDS 249 8.2.2 CHIRAL MONODENTATE
PHOSPHITE LIGANDS 257 8.2.3 OTHER CHIRAL MONODENTATE PHOSPHORUS LIGANDS
262 8.2.4 MIXED CHIRAL MONODENTATE PHOSPHORUS LIGANDS 263 8.3 ASYMMETRIE
HYDROGENATION OF N,N-DIALKYL ENAMINES 264 8.4 CONDUSION AND OUTLOOK 269
REFERENCES 270 9 BIDENTATE LIGANDS FOER ENANTIOSELECTIVE ENAMIDE
REDUCTION 273 XIANG-PING HU AND ZHUO ZHENG 9.1 INTRODUCTION 273 9.2
CATALYTIC ENANTIOSELECTIVE HYDROGENATION OF ENAMIDES 274 9.2.1 SYNTHESIS
OF ENAMIDES 274 9.2.2 CATALYTIC ASYMMETRIE HYDROGENATION OF ACYDIC
ENAMIDES 276 9.2.2.1 CHIRAL PHOSPHOLANE LIGANDS FOR RH-CATALYZED
ASYMMETRIE HYDROGENATION 276 9.2.2.2 CHIRAL 1,4-DIPHOSPHINE LIGANDS FOR
RH-CATALYZED ASYMMETRIE HYDROGENATION 278 XIV CONTENTS 10.6 ASYMMETRIE
HYDROGENATION OF PYRIDINE DERIVATIVES 329 10.7 SUMMARY AND OUTLOOK 336
REFERENCES 337 11 ASYMMETRIE HYDROAMINATION 341 ALEXANDER L REZNICHENKO
AND KAI C. HULTZSCH 11.1 INTRODUCTION: SYNTHESIS OF AMINES VIA
HYDROAMINATION 341 11.2 HYDROAMINATION OF SIMPLE, NONACTIVATED ALKENES
342 11.2.1 INTERMOLECULAR HYDROAMINATION OF SIMPLE ALKENES 342 11.2.2
INTRAMOLECULAR ASYMMETRIE HYDROAMINATION OF SIMPLE AMINOALKENES 346
11.2.2.1 RARE EARTH METAL-BASED CATALYSTS 346 11.2.2.2 ALKALI
METAL-BASED CATALYSTS 353 11.2.2.3 GROUP 4 METAL-BASED CATALYSTS 356
11.2.2.4 ORGANOCATALYTIC ASYMMETRIC HYDROAMINATION 358 11.3
HYDROAMINATION OF DIENES, ALLENES, AND ALKYNES 360 11.3.1 INTERMOLECULAR
HYDROAMINATIONS 360 11.3.2 INTRAMOLECULAR REACTIONS 361 11.4
HYDROAMINATION WITH ENANTIOMERICAL PURE AMINES 363 11.4.1
HYDROAMINATIONS USING ACHIRAL CATALYSTS 363 11.4.2 KINETIC RESOLUTION OF
CHIRAL AMINOALKENES 366 11.5 SYNTHESIS OF CHIRAL AMINES VIA TANDEM
HYDROAMINATION/ HYDROSILYLATION 368 11.6 CONDUSIONS 369 11. CONTENTS XV
13.2 RECENT MECHANISTIC INSIGHTS 398 13.3 ASYMMETRIC AZA-MBH REACTION
400 13.4 CHIRAL AUXILIARY-INDUCED DIASTEREOSELECTIVE AZA-MBH REACTION
400 13.5 CHIRAL TERTIARY AMINE CATALYSTS 401 13.5.1 CINCHONA-DERIVED
BIFUNCTIONAL CATALYSTS 401 13.5.2 CHIRAL BINOL-DERIVED BIFUNCTIONAL
AMINE CATALYSTS 408 13.5.3 CHIRAL ACID/ACHIRAL AMINE 410 13.6 CHIRAL
PHOSPHINE CATALYSTS 411 13.7 CHIRAL BIFUNCTIONAL N-HETEROCYDIC CARBENES
418 13.8 CHIRAL IONIC LIQUIDS AS REACTION MEDIUM 419 13.9 AZA-MBH-TYPE
REACTION TO OBTAIN CHIRAL AMINES 419 13.10 STRATEGIES FOR THE REMOVAL OF
PROTECTING GROUPS 422 13.11 SELECTED TYPICAL EXPERIMENTAL PROCEDURES 423
13.11.1 TYPICAL PROCEDURES FOR LA-CATALYZED AZA-MBH REACTION OF METHYL
ACRYLATE WITH N-BENZYLIDENE-4-NITROBENZENESULFONAMIDE 423 13.11.2
TYPICAL PROCEDURES FOR SS-ICD-CATALYZED AZA-MBH REACTION OF MVKWITH
N-(P-ETHYLBENZENESULFONYL)BENZALDIMINE 423 13.11.3 TYPICAL PROCEDURES
FOR CHIRAL PHOSPHINE 23-CATALYZED AZA-MBH REACTION OF MVKWITH
N-(BENZYLIDENE)-4- CHLOROBENZENESULFONAMIDE 424 XVI CONTENTS 14.3.1 DKR
USING HYDROLYTIC ENZYMES AND RACEMIZATION CATALYSTS 444 14.3.2
DERACEMIZATION REACTIONS USING AMINE OXIDASES 448 14 A ASYMMETRIC
SYNTHESIS OF AMINES USING TRANSAMINASES 450 14.5 CONCLUSIONS AND FUTURE
PERSPECTIVES 455 REFERENCES 457 APPENDIX: SOLUTION 461 INDEX 479 |
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| spelling | Chiral amine synthesis methods, developments and applications ed. by Thomas C. Nugent Weinheim Wiley-VCH 2010 XXV, 494 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Amine (DE-588)4001705-9 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Chirale Verbindungen (DE-588)4348527-3 gnd rswk-swf Amine (DE-588)4001705-9 s Chirale Verbindungen (DE-588)4348527-3 s Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Nugent, Thomas C. edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3348540&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=020201108&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Chiral amine synthesis methods, developments and applications Amine (DE-588)4001705-9 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| subject_GND | (DE-588)4001705-9 (DE-588)4135603-2 (DE-588)4348527-3 |
| title | Chiral amine synthesis methods, developments and applications |
| title_auth | Chiral amine synthesis methods, developments and applications |
| title_exact_search | Chiral amine synthesis methods, developments and applications |
| title_full | Chiral amine synthesis methods, developments and applications ed. by Thomas C. Nugent |
| title_fullStr | Chiral amine synthesis methods, developments and applications ed. by Thomas C. Nugent |
| title_full_unstemmed | Chiral amine synthesis methods, developments and applications ed. by Thomas C. Nugent |
| title_short | Chiral amine synthesis |
| title_sort | chiral amine synthesis methods developments and applications |
| title_sub | methods, developments and applications |
| topic | Amine (DE-588)4001705-9 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| topic_facet | Amine Asymmetrische Synthese Chirale Verbindungen |
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