Hydrogen bonding in organic synthesis:
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| Other Authors: | |
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2009
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XII, 383 S. graph. Darst. |
| ISBN: | 9783527318957 |
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Record in the Search Index
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| adam_text |
CONTENTS PREFACE IX LIST OF CONTRIBUTORS XI 1 INTRODUCTION 1 PETRI PINKO
1.1 INTRODUCTION 1 1.2 HYDROGEN BONDING IN ORGANIC SYNTHESIS 3
REFERENCES 4 2 HYDROGEN-BOND CATALYSIS OR BRANSTED-ACID CATALYSIS?
CENERAI CONSIDERATIONS 5 TAKAHIKO AKIYAMA 2.1 INTRODUCTION 5 2.2 WHAT IS
THE HYDROGEN BOND? 6 2.3 HYDROGEN-BOND CATALYSIS OR BRANSTED-ACID
CATALYSIS 7 2.4 BRANSTED-ACID CATALYSIS 9 2.5 HYDROGEN-BOND CATALYSIS 11
REFERENCES 13 3 COMPUTATIONAL STUDIES OF ORGANOCATATYTK PROCESSES BASED
ON HYDROGEN BONDING 15 ALBRECHT BERKESSEL AND KERSTIN ETZENBACH-EFFEN
3.1 INTRODUCTION 15 3.1.1 CATALYTIC FUNCTIONS OF HYDROGEN BONDS 18 3.2
DYNAMIC KINETIC RESOLUTION (DKR) OF AZLACTONES-THIOUREAS CAN ACT AS
OXYANION HOLES COMPARABLE TO SERINE HYDROLASES 19 3.2.1 THE CALCULATED
REACTION PATH OF THE ALCOHOLYTIC RING OPENING OF AZLACTONES 19 3.2.2 HOW
HYDROGEN BONDS DETERMINE THE ENANTIOSELECTIVITY OF THE ALCOHOLYTIC
AZLACTONE OPENING 23 3.3 ON THE BIFUNCTIONALITY OF CHIRAL
THIOUREA-TERT-AMINE-BASED ORGANOCATALYSTS BIBLIOGRAFISCHE INFORMATIONEN
HTTP://D-NB.INFO/991677315 DIGITALISIERT DURCH VI I CONTENTS 3.4
DRAMATIC ACCELERATION OF OLEFM EPOXIDATION IN FLUORINATED ALCOHOLS:
ACTIVATION OF HYDROGEN PEROXIDE BY MULTIPLE HYDROGEN BOND NETWORKS 29
3.4.1 HYDROGEN BOND DONOR FEATURES OF HFIP 30 3.4.2 THE CATALYTIC
ACTIVITY OF HFIP IN THE EPOXIDATION REACTION 30 3.5 TADDOL-PROMOTED
ENANTIOSELECTIVE HETERO-DIELS-ALDER REACTION OF DANISHEFSKY'S DIENE WITH
BENZALDEHYDE-ANOTHER EXAMPLE FOR CATALYSIS BY COOPERATIVE HYDROGEN
BONDING 37 3.6 EPILOG 40 REFERENCES 41 4 OXYANION HOLES AND THEIR MIMICS
43 PETRI PINKO, SANNA RAPAKKO, AND RIK K. WIERENGA 4.1 INTRODUCTION 43
4.1.1 WHAT ARE OXYANION HOLES? 44 4.1.2 CONTRIBUTIONS OF OXYANION HOLES
TO CATALYSIS 44 4.1.3 PROPERTIES OF HYDROGEN BONDS OF OXYANION HOLES 47
4.2 A MORE DETAILED DESCRIPTION OF THE TWO CLASSES OF OXYANION HOLES IN
ENZYMES 49 4.2.1 A HISTORICAL PERSPECTIVE 49 4.2.2 OXYANION HOLES WITH
TETRAHEDRAL INTERMEDIATES 52 4.2.3 OXYANION HOLES WITH ENOLATE
INTERMEDIATES 56 4.2.3.1 EXAMPLES OF ENOLATE OXYANION HOLES 58 4. VII
5.2.4 ASYMMETRIE COUNTERANION-DIRECTED CATALYSIS 98 5.3 N-H HYDROGEN
BOND CATALYSTS 99 5.3.1 GUANIDINE ORGANIC BASE 99 5.3.2 AMMONIUM SALT
CATALYSIS 106 5.3.3 CHIRAL TETRAAMINOPHOSPHONIUM SALT 109 5.4 COMBINED
ACID CATALYSIS 109 5.4.1 BRANSTED-ACID-ASSISTED BRENSTED ACID CATALYSIS
110 5.4.1.1 DIOL ACTIVATION OF CARBONYL ELECTROPHILES 111 5.4.1.2 DIOL
ACTIVATION OF OTHER ELECTROPHILES 116 5.4.1.3 MISCELLANEOUS BBA AND
RELATED SYSTEMS 120 5.4.2 LEWIS-ACID-ASSISTED BRANSTED ACID CATALYSIS
122 5.4.3 BRANSTED-ACID-ASSISTED LEWIS ACID CATALYSIS (CATIONIC
OXAZABOROLIDINE) 126 5.4.3.1 DIELS-ALDER REACTIONS 126 5.4.3.2
MISCELLANEOUS REACTIONS 132 REFERENCES 136 6 (THIO)UREA ORGANOCATALYSTS
141 MIKE KOTKE AND PETER R. SCHREINER 6.1 INTRODUCTION AND BACKGROUND
141 6.2 SYNTHETIC APPLICATIONS OF HYDROGEN-BONDING (THIO)UREA
ORGANOCATALYSTS 149 6.2.1 NONSTEREOSELECTIVE (THIO)UREA ORGANOCATALYSTS
149 6.2.1.1 PRIVILEGED HYDROGEN-BONDING N,JV-BIS-
[3,5-(TRIFLUOROMETHYL)PHENYL]THIOUREA 149 6.2.1. VILI I CONTENTS 7.2.1
THERMODYNAMIC CONTROL OF STEREOCHEMISTRY 353 7.2.1.1 PINNATOXINA 353
7.2.1.2 AZASPIRACID-1 355 7.2.2 KINETIC CONTROL STEREOCHEMISTRY 355
7.2.2.1 PANCRATISTATIN 355 7.2.2.2 TUNICAMYCINS 357 7.2.2.3 CALLYSTATIN
358 7.2.2.4 RESORCYLIDES 359 7.2.2.5 STRYCHNOFOLINE 361 7.2.2.6 ASIALO
GM! 361 7.2.3 ACTIVATION/DEACTIVATION OF REACTIONS 362 7.2.3.1
RISHIRILIDEB 362 7.2.3.2 2-DESOXYSTEMODIONE 363 7.2.3.3 LEUCASCANDROLIDE
A 363 7.2.3.4 AZASPIRENE 364 7.3 INTERMOLECULAR HYDROGEN BONDINGS IN
TOTAL SYNTHESES 365 7.3.1 HENBEST EPOXIDATION 365 7.3.2 EPOXYQUINOLS 366
7.3.3 EPOXIDE-OPENING CASCADES 367 7.4 CONCLUSIONS 369 REFERENCES 369
INDEX 373 |
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| spelling | Hydrogen bonding in organic synthesis ed. by Petri M. Pihko Weinheim Wiley-VCH 2009 XII, 383 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Hydrogen bonding Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd rswk-swf Wasserstoffbrückenbindung (DE-588)4064787-0 gnd rswk-swf Wasserstoffbrückenbindung (DE-588)4064787-0 s Organische Synthese (DE-588)4075695-6 s DE-604 Pihko, Petri M. 1971- (DE-588)139525068 edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3191882&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=018667883&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Hydrogen bonding in organic synthesis Hydrogen bonding Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Wasserstoffbrückenbindung (DE-588)4064787-0 gnd |
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| title | Hydrogen bonding in organic synthesis |
| title_auth | Hydrogen bonding in organic synthesis |
| title_exact_search | Hydrogen bonding in organic synthesis |
| title_full | Hydrogen bonding in organic synthesis ed. by Petri M. Pihko |
| title_fullStr | Hydrogen bonding in organic synthesis ed. by Petri M. Pihko |
| title_full_unstemmed | Hydrogen bonding in organic synthesis ed. by Petri M. Pihko |
| title_short | Hydrogen bonding in organic synthesis |
| title_sort | hydrogen bonding in organic synthesis |
| topic | Hydrogen bonding Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Wasserstoffbrückenbindung (DE-588)4064787-0 gnd |
| topic_facet | Hydrogen bonding Organic compounds Synthesis Organische Synthese Wasserstoffbrückenbindung |
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