Holdings: Asymmetric organocatalysis

Asymmetric organocatalysis: new strategies, catalysts, and opportunities Volume 1

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Bibliographic Details
Other Authors:	Albrecht, Łukasz 1980- (Editor), Albrecht, Anna (Editor), Dell'Amico, Luca (Editor)
Format:	Book
Language:	English
Published:	Weinheim Wiley-VCH [2023]
Subjects:	Aufsatzsammlung
Online Access:	Inhaltsverzeichnis
Physical Description:	xiv, 348 Seiten Illustrationen, Diagramme
ISBN:	9783527351251

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adam_text	VII CONTENTS VOLUME 1 PREFACE XIII PART I NEW CATALYSTS AND ACTIVATION STRATEGIES IN ASYMMETRIC ORGANOCATALYSIS 1 1 NEW DEVELOPMENTS IN ENANTIOSELECTIVE BRONSTED ACID CATALYSIS WITH STRONG HYDROGEN BOND DONORS 3 CAROLINE DORSCH AND CHRISTOPH SCHNEIDER 1.1 INTRODUCTION 3 1.2 CHIRAL BINOL-PHOSPHORIC ACIDS IN DEHYDRATION REACTIONS 5 1.3 CHIRAL BINSA-AMMONIUM SALTS 9 1.4 CHIRAL CYCLOPENTADIENYL-BASED BRONSTED ACIDS 12 1.5 COMBINED THIOUREA-CARBOXYLIC ACIDS 14 1.6 DISULFONIMIDES 16 1.7 IMIDODIPHOSHORIC ACIDS 19 1.8 IMIDODIPHOSPHORIMIDATES 25 1.9 SILYLIUM ASYMMETRIC COUNTERION-DIRECTED CATALYSIS 29 1.10 SUMMARY AND CONCLUSIONS 37 ACKNOWLEDGMENTS 37 REFERENCES 37 2 ORGANOSUPERBASES - MOVING BEYOND CLASSICAL BRONSTED BASE CATALYSIS 43 AZUSA KONDOH AND MASAHIRO TERADA 2.1 INTRODUCTION 43 2.2 CHIRAL CYCLOPROPENIMINE CATALYSTS 46 2.3 CHIRAL TRIARYLIMINOPHOSPHORANE CATALYSTS 48 2.4 CHIRAL P1-PHOSPHAZENE CATALYSTS 52 2.5 CHIRAL HIGHER-ORDER PHOSPHAZENE CATALYSTS 58 2.6 OTHER CHIRAL STRONG BRONSTED BASE CATALYSTS 62 2.7 SUMMARY AND CONCLUSIONS 64 REFERENCES 65 VIII CONTENTS 3 ASYMMETRIC PHASE-TRANSFER CATALYSIS - FROM CLASSICAL APPLICATIONS TO NEW CONCEPTS 71 JAN OTEVREL AND MARIO WASER 3.1 3.2 3.2.1 3.2.2 3.2.3 3.3 3.3.1 3.3.2 3.3.3 3.3.4 3.3.5 3.3.6 3.3.7 3.3.8 3.3.9 3.3.10 3.3.11 3.3.12 INTRODUCTION 71 CLASSES OF ASYMMETRIC PTCS 73 CHIRAL CATION-BASED CATALYSTS 74 CHIRAL ANION-BASED CATALYSTS 78 UNCHARGED PTCS 80 APPLICATIONS OF CHIRAL PTCS 81 " CLASSICAL " APPLICATIONS OF QUATERNARY (AMM)-ONIUM SALTS 82 SN AR REACTIONS 83 UMPOLUNG OF IMINES 84 UTILIZATION OF ALLENOATES 86 INTRAMOLECULAR CARBO AND HETEROCYCLIZATION APPROACHES 87 INTERMOLECULAR CARBO AND HETEROCYCLIZATION APPROACHES 89 UTILIZATION OF O-, N-, AND S-NUCLEOPHILES 94 ELECTROPHILIC A-HETEROFUNCTIONALIZATION REACTIONS 99 PTC-CONTROLLED REACTIVITY OF F + AND F SPECIES 101 AMMONIUM (HYPO)-LODITE CATALYSIS 105 PTCS IN COMBINATION WITH PHOTOCHEMISTRY 106 BISGUANIDINIUM SALT-CATALYZED OXIDATIONS USING PERMANGANATE, TUNGSTATE 107 3.3.12.1 3.3.13 PTCS IN COMBINATION WITH TRANSITION METAL CATALYSIS 108 SYNOPSIS 108 REFERENCES 109 4 ASYMMETRIC ION-PAIRING AND H-BONDING CATALYSIS 121 ESTEBAN MATADOR, ROSARIO FERNANDEZ, JOSE M. LASSALETTA, AND DAVID MONGE 4.1 4.2 4.2.1 4.2.2 4.2.3 4.3 4.3.1 4.3.2 4.4 4.4.1 4.4.2 4.4.3 4.5 INTRODUCTION 121 ION-PAIR WITH CHIRAL CATALYST-BOUND SPECTATOR ANIONS 122 REACTIONS INVOLVING OXYGEN-STABILIZED CATIONS 122 REACTIONS INVOLVING NITROGEN-STABILIZED CATIONS 126 REACTIONS NOT INVOLVING HETEROATOM-STABILIZED CARBOCATIONS 132 ION-PAIR WITH CHIRAL CATALYST-BOUND REACTIVE IONS 134 CATALYST-BOUND ANION ACTING AS NUCLEOPHILE 134 CATALYST-BOUND OXY-ALLYL CATION ACTING AS ELECTROPHILE 136 ANION-BINDING CATALYSIS COMBINED WITH OTHER ACTIVATION MODES 137 MERGING ANION-BINDING WITH NUCLEOPHILIC CATALYSIS 137 MERGING ANION BINDING WITH AMINOCATALYSIS 140 MERGING ANION BINDING WITH PHOTOCHEMICAL ACTIVATIONS 142 SUMMARY AND CONCLUSIONS 143 REFERENCES 144 5 ISOTHIOUREA CATALYSIS - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 151 ALASTAIR J. NIMMO, CLAIRE M. YOUNG, AND ANDREW D. SMITH 5.1 INTRODUCTION 151 CONTENTS IX 5.2 ACYL TRANSFER REACTIONS 154 5.2.1 ACYLATIVE KINETIC RESOLUTIONS OF ALCOHOLS 154 5.2.2 ACYLATIVE DESYMMETRIZATION OF DIOLS 158 5.2.3 N-ACYLATION 159 5.2.4 KINETIC RESOLUTIONS OF CHIRAL CARBOXYLIC ACID DERIVATIVES 161 5.2.5 DYNAMIC KINETIC RESOLUTIONS 162 5.2.6 ENANTIOSELECTIVE O-C ACYL TRANSFER 163 5.3 SILYL TRANSFER REACTIONS 165 5.4 A,P-UNSATURATED ACYL AMMONIUM INTERMEDIATES 166 5.4.1 MICHAEL ADDITION-ANNULATION 166 5.4.2 CASCADE REACTIONS 170 5.4.3 CYCLOADDITIONS 174 5.4.4 CATALYST TURNOVER BY ARYLOXIDE 175 5.5 C(1)-AMMONIUM ENOLATES 177 5.5.1 SURFACE MODIFICATION 180 5.5.2 CATALYST TURNOVER BY ARYLOXIDE 181 5.6 DIASTEREO AND ENANTIOSELECTIVE [2,3]-SIGMATROPIC REARRANGEMENTS 188 5.7 SOLID-SUPPORTED CATALYSIS 190 5.8 SUMMARY AND CONCLUSIONS 193 REFERENCES 193 6 HALOGEN-BONDING ORGANOCATALYSIS - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 203 MIKK KAASIK AND TDNIS KANGER 6.1 INTRODUCTION 203 6.2 XB DONORS AS ORGANOCATALYSTS 204 6.3 SOLELY XB CATALYTIC ACTIVATION IN COMBINATION WITH ASYMMETRIC COUNTERION-DIRECTED CATALYSIS 207 6.4 ASYMMETRIC CATALYSIS THROUGH SOLELY XB CATALYTIC ACTIVATION 209 6.5 BIFUNCTIONAL CATALYSTS AND CO-CATALYTIC SYSTEMS UTILIZING XB ACTIVATION IN ASYMMETRIC CATALYSIS 211 6.6 TOPICS RELATED TO ASYMMETRIC XB CATALYSIS 215 6.7 FUTURE PERSPECTIVES 217 6.8 SUMMARY AND CONCLUSIONS 219 REFERENCES 220 7 MERGING ORGANOCATALYSIS WITH LIGHT - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 225 JOSE ALEMAN, LEYRE MARZO, JOSE A. FERNANDEZ-SALAS, AND ALBERTO FRAILE 7.1 INTRODUCTION 225 7.2 COVALENT CATALYSIS 227 7.2.1 DUAL AMINE-PHOTOREDOX CATALYSIS 228 7.2.1.1 DUAL CATALYSIS: ENAMINE-BASED STRATEGY 228 7.2.1.2 DUAL CATALYSIS: IMINIUM-BASED STRATEGY 233 7.2.2 AMINES AS ORGANO-PHOTOCATALYSTS 235 7.2.2.1 ENAMINE PHOTO-ORGANOCATALYSIS 235 X CONTENTS 7.2.2.2 7.2.3 7.3 IMINIUM PHOTO-ORGANOCATALYSIS 238 DUAL PHOTOREDOX-N-HETEROCYCLIC CARBENE CATALYSIS 240 ASYMMETRIC PHOTOCATALYSIS MEDIATED BY NON-COVALENT ORGANOCATALYSIS 241 7.3.1 7.3.1.1 7.3.1.2 7.3.1.3 7.3.2 7.3.2.1 7.3.2.2 7.4 STEREOINDUCTION IN THE GROUND STATE 241 HYDROGEN BOND ACTIVATION 241 ION PAIR ACTIVATION 245 LEWIS BASE ACTIVATION 246 STEREOINDUCTION IN THE EXCITED STATE 247 HYDROGEN BOND ACTIVATION 247 ION PAIR ACTIVATION MODE 249 CONCLUSIONS 250 REFERENCES 250 8 ASYMMETRIC ELECTROCHEMICAL ORGANOCATALYSIS: NEW OPPORTUNITIES FOR SYNTHESIS 259 YINGDONG DUAN, QIFENG UN, AND SANZHONG LUO 8.1 8.2 8.2.1 8.2.2 8.2.3 8.2.4 8.2.5 8.3 INTRODUCTION 259 ORGANOCATALYSIS IN ASYMMETRIC ELECTROCHEMICAL REACTIONS 260 NATURAL ALKALOIDS 260 P CYCLODEXTRINS 261 IMINIUM SALTS 262 AMINOCATALYSTS 263 HYDROGEN-BONDING CATALYSTS 267 SUMMARY AND OUTLOOK 268 REFERENCES 269 9 SYNERGISTIC ORGANO-ORGANOCATALYSIS 271 FABIO PESCIAIOLI, VALERIA NORI, ARIANNA SINIBALDI, AND ARMANDO CARLONE 9.1 9.1.1 9.1.2 9.1.3 9.1.4 9.1.5 9.1.6 9.2 INTRODUCTION 271 ENAMINE IN SYNERGISTIC ORGANOCATALYSIS 272 IMINIUM ION IN SYNERGISTIC ORGANOCATALYSIS 279 HYDROGEN BONDING IN SYNERGISTIC ORGANOCATALYSIS 286 ACIDS AND BASES IN SYNERGISTIC ORGANOCATALYSIS 293 PHASE-TRANSFER CATALYSIS IN SYNERGISTIC ORGANOCATALYSIS 298 N-HETEROCYCLIC CARBENES IN SYNERGISTIC ORGANOCATALYSIS 299 SUMMARY AND CONCLUSIONS 309 REFERENCES 309 10 MERGING ORGANOCATALYSIS WITH METALS - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 319 ROMON RIOS 10.1 10.2 10.3 INTRODUCTION 319 METAL AND ENAMINE CATALYSIS 320 COMBINATION OF A METAL CATALYSIS AND IMINIUM CHEMISTRY 328 CONTENTS XI 10.4 TRANSITION METAL AND ORGANOCASCADE (IMINIUM/ENAMINE) ACTIVATION 331 10.5 MERGING THE NHC AND METAL CATALYSES 339 10.6 SUMMARY AND CONCLUSIONS 343 REFERENCES 343 VOLUME 2 PREFACE XV 11 IMMOBILIZED ORGANOCATALYSIS FOR ENANTIOSELECTIVE CONTINUOUS FLOW PROCESSES 349 CARLES RODRIGUEZ-ESCRICH AND MIQUEL A. PERICAS 12 MECHANOCHEMISTRY AND HIGH-PRESSURE TECHNIQUES IN ASYMMETRIC ORGANOCATALYSIS 393 RAFAT KOWALCZYK 13 ORGANOCATALYTIC REACTIONS UNDER NONTRADITIONAL CONDITIONS 433 C. GABRIELA AVILA-ORTIZ, ALBERTO VEGA-PENALOZA, AND EUSEBIO JUARISTI PART II NEW ORGANOCATALYTIC SYNTHETIC METHODOLOGIES 455 14 MERGING ORGANOCATALYSIS WITH VINYLOGY - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 457 CLAUDIO CURTI, ANDREA SARTORI, LUCIA BATTISTINI, AND FRANCA ZANARDI 15 ORGANOCATALYTIC UMPOLUNG STRATEGIES: BEYOND CLASSICAL REACTIVITY PATTERNS 497 SAYAN SHEE, ARGHYA GHOSH, AND AKKATTU T. BIJU 16 DEAROMATIVE ORGANOCATALYTIC STRATEGIES 539 XUE SONG, ZHI-CHAO CHEN, WEI DU, AND YING-CHUN CHEN 17 FROM ORGANOCATALYTIC CYCLOADDITIONS TO ASYMMETRIC HIGHER-ORDER CYCLOADDITIONS 577 KARL ANKER JORGENSEN AND K. N. HOUK 18 ASYMMETRIC ORGANOCATALYSIS - FROM A PROCESS DEVELOPMENT PERSPECTIVE 601 HAO JIANG, BJORN GSCHWEND, AND YANG LI *II I CONTENTS PART III MECHANISMS OF ORGANOCATALYTIC REACTIONS 633 19 COMPUTATIONAL STUDIES - A USEFUL TOOL IN ELUCIDATION OF MECHANISMS OF ORGANOCATALYTIC REACTIONS 635 SIMARPREET SINGH, JORGE DOURADO, AND REBECCA L. DAVIS 20 A TUTORIAL ON KINETIC-ASSISTED MECHANISTIC ANALYSIS IN ASYMMETRIC AMINOCATALYSIS 657 JORDI BURES, ALAN ARMSTRONG, AND DONNA G. BLACKMOND 21 MAYR LINEAR FREE ENERGY RELATIONSHIP: A POWERFUL TOOL FOR UNDERSTANDING AMINOCATALYZED REACTIONS 679 SAMI LAKHDAR INDEX 701
adam_txt	VII CONTENTS VOLUME 1 PREFACE XIII PART I NEW CATALYSTS AND ACTIVATION STRATEGIES IN ASYMMETRIC ORGANOCATALYSIS 1 1 NEW DEVELOPMENTS IN ENANTIOSELECTIVE BRONSTED ACID CATALYSIS WITH STRONG HYDROGEN BOND DONORS 3 CAROLINE DORSCH AND CHRISTOPH SCHNEIDER 1.1 INTRODUCTION 3 1.2 CHIRAL BINOL-PHOSPHORIC ACIDS IN DEHYDRATION REACTIONS 5 1.3 CHIRAL BINSA-AMMONIUM SALTS 9 1.4 CHIRAL CYCLOPENTADIENYL-BASED BRONSTED ACIDS 12 1.5 COMBINED THIOUREA-CARBOXYLIC ACIDS 14 1.6 DISULFONIMIDES 16 1.7 IMIDODIPHOSHORIC ACIDS 19 1.8 IMIDODIPHOSPHORIMIDATES 25 1.9 SILYLIUM ASYMMETRIC COUNTERION-DIRECTED CATALYSIS 29 1.10 SUMMARY AND CONCLUSIONS 37 ACKNOWLEDGMENTS 37 REFERENCES 37 2 ORGANOSUPERBASES - MOVING BEYOND CLASSICAL BRONSTED BASE CATALYSIS 43 AZUSA KONDOH AND MASAHIRO TERADA 2.1 INTRODUCTION 43 2.2 CHIRAL CYCLOPROPENIMINE CATALYSTS 46 2.3 CHIRAL TRIARYLIMINOPHOSPHORANE CATALYSTS 48 2.4 CHIRAL P1-PHOSPHAZENE CATALYSTS 52 2.5 CHIRAL HIGHER-ORDER PHOSPHAZENE CATALYSTS 58 2.6 OTHER CHIRAL STRONG BRONSTED BASE CATALYSTS 62 2.7 SUMMARY AND CONCLUSIONS 64 REFERENCES 65 VIII CONTENTS 3 ASYMMETRIC PHASE-TRANSFER CATALYSIS - FROM CLASSICAL APPLICATIONS TO NEW CONCEPTS 71 JAN OTEVREL AND MARIO WASER 3.1 3.2 3.2.1 3.2.2 3.2.3 3.3 3.3.1 3.3.2 3.3.3 3.3.4 3.3.5 3.3.6 3.3.7 3.3.8 3.3.9 3.3.10 3.3.11 3.3.12 INTRODUCTION 71 CLASSES OF ASYMMETRIC PTCS 73 CHIRAL CATION-BASED CATALYSTS 74 CHIRAL ANION-BASED CATALYSTS 78 UNCHARGED PTCS 80 APPLICATIONS OF CHIRAL PTCS 81 " CLASSICAL " APPLICATIONS OF QUATERNARY (AMM)-ONIUM SALTS 82 SN AR REACTIONS 83 UMPOLUNG OF IMINES 84 UTILIZATION OF ALLENOATES 86 INTRAMOLECULAR CARBO AND HETEROCYCLIZATION APPROACHES 87 INTERMOLECULAR CARBO AND HETEROCYCLIZATION APPROACHES 89 UTILIZATION OF O-, N-, AND S-NUCLEOPHILES 94 ELECTROPHILIC A-HETEROFUNCTIONALIZATION REACTIONS 99 PTC-CONTROLLED REACTIVITY OF F + AND F SPECIES 101 AMMONIUM (HYPO)-LODITE CATALYSIS 105 PTCS IN COMBINATION WITH PHOTOCHEMISTRY 106 BISGUANIDINIUM SALT-CATALYZED OXIDATIONS USING PERMANGANATE, TUNGSTATE 107 3.3.12.1 3.3.13 PTCS IN COMBINATION WITH TRANSITION METAL CATALYSIS 108 SYNOPSIS 108 REFERENCES 109 4 ASYMMETRIC ION-PAIRING AND H-BONDING CATALYSIS 121 ESTEBAN MATADOR, ROSARIO FERNANDEZ, JOSE M. LASSALETTA, AND DAVID MONGE 4.1 4.2 4.2.1 4.2.2 4.2.3 4.3 4.3.1 4.3.2 4.4 4.4.1 4.4.2 4.4.3 4.5 INTRODUCTION 121 ION-PAIR WITH CHIRAL CATALYST-BOUND SPECTATOR ANIONS 122 REACTIONS INVOLVING OXYGEN-STABILIZED CATIONS 122 REACTIONS INVOLVING NITROGEN-STABILIZED CATIONS 126 REACTIONS NOT INVOLVING HETEROATOM-STABILIZED CARBOCATIONS 132 ION-PAIR WITH CHIRAL CATALYST-BOUND REACTIVE IONS 134 CATALYST-BOUND ANION ACTING AS NUCLEOPHILE 134 CATALYST-BOUND OXY-ALLYL CATION ACTING AS ELECTROPHILE 136 ANION-BINDING CATALYSIS COMBINED WITH OTHER ACTIVATION MODES 137 MERGING ANION-BINDING WITH NUCLEOPHILIC CATALYSIS 137 MERGING ANION BINDING WITH AMINOCATALYSIS 140 MERGING ANION BINDING WITH PHOTOCHEMICAL ACTIVATIONS 142 SUMMARY AND CONCLUSIONS 143 REFERENCES 144 5 ISOTHIOUREA CATALYSIS - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 151 ALASTAIR J. NIMMO, CLAIRE M. YOUNG, AND ANDREW D. SMITH 5.1 INTRODUCTION 151 CONTENTS IX 5.2 ACYL TRANSFER REACTIONS 154 5.2.1 ACYLATIVE KINETIC RESOLUTIONS OF ALCOHOLS 154 5.2.2 ACYLATIVE DESYMMETRIZATION OF DIOLS 158 5.2.3 N-ACYLATION 159 5.2.4 KINETIC RESOLUTIONS OF CHIRAL CARBOXYLIC ACID DERIVATIVES 161 5.2.5 DYNAMIC KINETIC RESOLUTIONS 162 5.2.6 ENANTIOSELECTIVE O-C ACYL TRANSFER 163 5.3 SILYL TRANSFER REACTIONS 165 5.4 A,P-UNSATURATED ACYL AMMONIUM INTERMEDIATES 166 5.4.1 MICHAEL ADDITION-ANNULATION 166 5.4.2 CASCADE REACTIONS 170 5.4.3 CYCLOADDITIONS 174 5.4.4 CATALYST TURNOVER BY ARYLOXIDE 175 5.5 C(1)-AMMONIUM ENOLATES 177 5.5.1 SURFACE MODIFICATION 180 5.5.2 CATALYST TURNOVER BY ARYLOXIDE 181 5.6 DIASTEREO AND ENANTIOSELECTIVE [2,3]-SIGMATROPIC REARRANGEMENTS 188 5.7 SOLID-SUPPORTED CATALYSIS 190 5.8 SUMMARY AND CONCLUSIONS 193 REFERENCES 193 6 HALOGEN-BONDING ORGANOCATALYSIS - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 203 MIKK KAASIK AND TDNIS KANGER 6.1 INTRODUCTION 203 6.2 XB DONORS AS ORGANOCATALYSTS 204 6.3 SOLELY XB CATALYTIC ACTIVATION IN COMBINATION WITH ASYMMETRIC COUNTERION-DIRECTED CATALYSIS 207 6.4 ASYMMETRIC CATALYSIS THROUGH SOLELY XB CATALYTIC ACTIVATION 209 6.5 BIFUNCTIONAL CATALYSTS AND CO-CATALYTIC SYSTEMS UTILIZING XB ACTIVATION IN ASYMMETRIC CATALYSIS 211 6.6 TOPICS RELATED TO ASYMMETRIC XB CATALYSIS 215 6.7 FUTURE PERSPECTIVES 217 6.8 SUMMARY AND CONCLUSIONS 219 REFERENCES 220 7 MERGING ORGANOCATALYSIS WITH LIGHT - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 225 JOSE ALEMAN, LEYRE MARZO, JOSE A. FERNANDEZ-SALAS, AND ALBERTO FRAILE 7.1 INTRODUCTION 225 7.2 COVALENT CATALYSIS 227 7.2.1 DUAL AMINE-PHOTOREDOX CATALYSIS 228 7.2.1.1 DUAL CATALYSIS: ENAMINE-BASED STRATEGY 228 7.2.1.2 DUAL CATALYSIS: IMINIUM-BASED STRATEGY 233 7.2.2 AMINES AS ORGANO-PHOTOCATALYSTS 235 7.2.2.1 ENAMINE PHOTO-ORGANOCATALYSIS 235 X CONTENTS 7.2.2.2 7.2.3 7.3 IMINIUM PHOTO-ORGANOCATALYSIS 238 DUAL PHOTOREDOX-N-HETEROCYCLIC CARBENE CATALYSIS 240 ASYMMETRIC PHOTOCATALYSIS MEDIATED BY NON-COVALENT ORGANOCATALYSIS 241 7.3.1 7.3.1.1 7.3.1.2 7.3.1.3 7.3.2 7.3.2.1 7.3.2.2 7.4 STEREOINDUCTION IN THE GROUND STATE 241 HYDROGEN BOND ACTIVATION 241 ION PAIR ACTIVATION 245 LEWIS BASE ACTIVATION 246 STEREOINDUCTION IN THE EXCITED STATE 247 HYDROGEN BOND ACTIVATION 247 ION PAIR ACTIVATION MODE 249 CONCLUSIONS 250 REFERENCES 250 8 ASYMMETRIC ELECTROCHEMICAL ORGANOCATALYSIS: NEW OPPORTUNITIES FOR SYNTHESIS 259 YINGDONG DUAN, QIFENG UN, AND SANZHONG LUO 8.1 8.2 8.2.1 8.2.2 8.2.3 8.2.4 8.2.5 8.3 INTRODUCTION 259 ORGANOCATALYSIS IN ASYMMETRIC ELECTROCHEMICAL REACTIONS 260 NATURAL ALKALOIDS 260 P CYCLODEXTRINS 261 IMINIUM SALTS 262 AMINOCATALYSTS 263 HYDROGEN-BONDING CATALYSTS 267 SUMMARY AND OUTLOOK 268 REFERENCES 269 9 SYNERGISTIC ORGANO-ORGANOCATALYSIS 271 FABIO PESCIAIOLI, VALERIA NORI, ARIANNA SINIBALDI, AND ARMANDO CARLONE 9.1 9.1.1 9.1.2 9.1.3 9.1.4 9.1.5 9.1.6 9.2 INTRODUCTION 271 ENAMINE IN SYNERGISTIC ORGANOCATALYSIS 272 IMINIUM ION IN SYNERGISTIC ORGANOCATALYSIS 279 HYDROGEN BONDING IN SYNERGISTIC ORGANOCATALYSIS 286 ACIDS AND BASES IN SYNERGISTIC ORGANOCATALYSIS 293 PHASE-TRANSFER CATALYSIS IN SYNERGISTIC ORGANOCATALYSIS 298 N-HETEROCYCLIC CARBENES IN SYNERGISTIC ORGANOCATALYSIS 299 SUMMARY AND CONCLUSIONS 309 REFERENCES 309 10 MERGING ORGANOCATALYSIS WITH METALS - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 319 ROMON RIOS 10.1 10.2 10.3 INTRODUCTION 319 METAL AND ENAMINE CATALYSIS 320 COMBINATION OF A METAL CATALYSIS AND IMINIUM CHEMISTRY 328 CONTENTS XI 10.4 TRANSITION METAL AND ORGANOCASCADE (IMINIUM/ENAMINE) ACTIVATION 331 10.5 MERGING THE NHC AND METAL CATALYSES 339 10.6 SUMMARY AND CONCLUSIONS 343 REFERENCES 343 VOLUME 2 PREFACE XV 11 IMMOBILIZED ORGANOCATALYSIS FOR ENANTIOSELECTIVE CONTINUOUS FLOW PROCESSES 349 CARLES RODRIGUEZ-ESCRICH AND MIQUEL A. PERICAS 12 MECHANOCHEMISTRY AND HIGH-PRESSURE TECHNIQUES IN ASYMMETRIC ORGANOCATALYSIS 393 RAFAT KOWALCZYK 13 ORGANOCATALYTIC REACTIONS UNDER NONTRADITIONAL CONDITIONS 433 C. GABRIELA AVILA-ORTIZ, ALBERTO VEGA-PENALOZA, AND EUSEBIO JUARISTI PART II NEW ORGANOCATALYTIC SYNTHETIC METHODOLOGIES 455 14 MERGING ORGANOCATALYSIS WITH VINYLOGY - NEW OPPORTUNITIES FOR ASYMMETRIC SYNTHESIS 457 CLAUDIO CURTI, ANDREA SARTORI, LUCIA BATTISTINI, AND FRANCA ZANARDI 15 ORGANOCATALYTIC UMPOLUNG STRATEGIES: BEYOND CLASSICAL REACTIVITY PATTERNS 497 SAYAN SHEE, ARGHYA GHOSH, AND AKKATTU T. BIJU 16 DEAROMATIVE ORGANOCATALYTIC STRATEGIES 539 XUE SONG, ZHI-CHAO CHEN, WEI DU, AND YING-CHUN CHEN 17 FROM ORGANOCATALYTIC CYCLOADDITIONS TO ASYMMETRIC HIGHER-ORDER CYCLOADDITIONS 577 KARL ANKER JORGENSEN AND K. N. HOUK 18 ASYMMETRIC ORGANOCATALYSIS - FROM A PROCESS DEVELOPMENT PERSPECTIVE 601 HAO JIANG, BJORN GSCHWEND, AND YANG LI *II I CONTENTS PART III MECHANISMS OF ORGANOCATALYTIC REACTIONS 633 19 COMPUTATIONAL STUDIES - A USEFUL TOOL IN ELUCIDATION OF MECHANISMS OF ORGANOCATALYTIC REACTIONS 635 SIMARPREET SINGH, JORGE DOURADO, AND REBECCA L. DAVIS 20 A TUTORIAL ON KINETIC-ASSISTED MECHANISTIC ANALYSIS IN ASYMMETRIC AMINOCATALYSIS 657 JORDI BURES, ALAN ARMSTRONG, AND DONNA G. BLACKMOND 21 MAYR LINEAR FREE ENERGY RELATIONSHIP: A POWERFUL TOOL FOR UNDERSTANDING AMINOCATALYZED REACTIONS 679 SAMI LAKHDAR INDEX 701
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illustrated	Illustrated
index_date	2024-07-03T21:14:15Z
indexdate	2025-01-10T17:14:04Z
institution	BVB
isbn	9783527351251
language	English
oai_aleph_id	oai:aleph.bib-bvb.de:BVB01-033998858
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physical	xiv, 348 Seiten Illustrationen, Diagramme
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publisher	Wiley-VCH
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spelling	Asymmetric organocatalysis new strategies, catalysts, and opportunities Volume 1 edited by Łukasz Albrecht, Anna Albrecht, and Luca Dell'Amico Weinheim Wiley-VCH [2023] xiv, 348 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier (DE-588)4143413-4 Aufsatzsammlung gnd-content Albrecht, Łukasz 1980- (DE-588)1281118400 edt Albrecht, Anna (DE-588)1281118915 edt Dell'Amico, Luca (DE-588)1281121010 edt (DE-604)BV048678115 1 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033998858&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis
spellingShingle	Asymmetric organocatalysis new strategies, catalysts, and opportunities
subject_GND	(DE-588)4143413-4
title	Asymmetric organocatalysis new strategies, catalysts, and opportunities
title_auth	Asymmetric organocatalysis new strategies, catalysts, and opportunities
title_exact_search	Asymmetric organocatalysis new strategies, catalysts, and opportunities
title_exact_search_txtP	Asymmetric organocatalysis new strategies, catalysts, and opportunities
title_full	Asymmetric organocatalysis new strategies, catalysts, and opportunities Volume 1 edited by Łukasz Albrecht, Anna Albrecht, and Luca Dell'Amico
title_fullStr	Asymmetric organocatalysis new strategies, catalysts, and opportunities Volume 1 edited by Łukasz Albrecht, Anna Albrecht, and Luca Dell'Amico
title_full_unstemmed	Asymmetric organocatalysis new strategies, catalysts, and opportunities Volume 1 edited by Łukasz Albrecht, Anna Albrecht, and Luca Dell'Amico
title_short	Asymmetric organocatalysis
title_sort	asymmetric organocatalysis new strategies catalysts and opportunities
title_sub	new strategies, catalysts, and opportunities
topic_facet	Aufsatzsammlung
url	http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033998858&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
volume_link	(DE-604)BV048678115
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