Organic stereochemistry: experimental and computational methods
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH Verlag GmbH & Co. KGaA
[2015]
|
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XV, 318 Seiten Illustrationen, Diagramme |
| ISBN: | 9783527338221 9783527688166 |
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MARC
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Record in the Search Index
| _version_ | 1809771816991850496 |
|---|---|
| adam_text |
CONTENTS
PREFACE IX
ACKNOWLEDGMENTS XI
LIST OF ABBREVIATIONS XIII
PART I FUNDAMENTALS 1
1 CHIRALITY 3
1.1 INTRODUCTION 3
1.2 TETRAHEDRON OF CARBON 9
1.2.1 TERPENOIDS 9
1.2.2 FLAVONOIDS 13
1.2.3 ALKALOIDS 14
1.2.4 STEROIDS 16
1.2.5 GLYCOSIDES 17
1.2.6 OTHERS 18
1.3 OTHER STEREOGENIC CENTERS 19
1.4 OPTICAL CHARACTERISTICS 23
1.4.1 MEASUREMENT OF OR 24
1.4.2 ECD AND ITS DEFINITION 25
1.4.3 OUTLINE OF VCD 26
1.4.4 OUTLINE OF ROA 27
REFERENCES 28
2 NON-OPTICAL METHOD IN CONFIGURATION STUDY 31
2.1
13
C NMR SPECTRA 31
2.1.1 NMR AND ATOMIC STRUCTURE 31
2.1.2
13
C NMR CALCULATION 32
2.1.3 'H NMR 34
2.1.4
13
C NMR PREDICTION AND CONFORMATIONAL SEARCH 34
2.2 X-RAY DIFFRACTION AND MOSHER METHOD 41
2.2.1 X-RAY DIFFRACTION 41
2.2.2 MOSHER METHOD 44
2.3 TRANSITION STATE ENERGY AND CHIRALITY SELECTIVITY 51
HTTP://D-NB.INFO/1065330804
VII
CONTENTS
2.4
2.4.1
2.4.2
2.4.3
2.4.4
PART II
3
3.1
3.2
3.3
3.3.1
3.3.2
3.3.2.1
3.3.2.2
3.4
3.5
3.5.1
3.5.2
3.5.3
3.5.4
4
4.1
4.2
4.3
4.4
4.5
4.5.1
4.5.2
4.5.3
5
5.1
5.2
5.2.1
5.2.2
5.3
5.4
5.4.1
SEPARATION OF CHIRAL COMPOUNDS 53
CHIRAL ORGANIC BASES 53
CHIRAL ORGANIC ACIDS S3
CHIRAL ORGANIC ALCOHOLS 53
OTHERS 54
REFERENCES 55
TECHNIQUES 57
OPTICAL ROTATION (ROTATORY DISPERSION, ORD) 59
INTRODUCTION 59
QUANTUM THEORY 59
MATRIX MODEL 63
MATRIX BASIS 65
EXPLANATION OF GENERAL OR CHARACTERISTICS
68
SAMPLE CALCULATIONS
68
CALCULATED VALUES IN SAME SERIES OF COMPOUNDS 73
ORD 77
APPLICATION 77
AC ASSIGNMENT FOR MONO-STEREOGENIC CENTER COMPOUNDS 79
MATRIX MODEL APPLICATION 80
AC ASSIGNMENT FOR POLY-STEREOGENIC CENTER COMPOUNDS 82
USING ORD METHOD 83
REFERENCES 84
ELECTRONIC CIRCULAR DICHROISM 87
EXCITON CHIRALITY CD 87
ECD CHARACTERISTICS FOR CHIRAL METALLIC COMPOUNDS 92
QUANTUM THEORY BASIS 94
PRINCIPLE USING ECD 95
APPLICATION 97
PROCEDURE TO DO ECD 97
ECD APPLICATION 97
UV CORRECTION 102
REFERENCES 105
VIBRATIONAL CIRCULAR DICHROISM AND RAMAN OPTICAL ACTIVITY 107
EXCITON CHIRALITY 108
QUANTUM THEORY BASIS 109
VCD AND IR 109
ROA AND RAMAN SCATTERING 110
PRINCIPLES USING VCD AND ROA 113
APPLICATION 115
VCD APPLICATION 115
CONTENTS I VII
5.4.2 ROA APPLICATION 124
REFERENCES 126
6 COMBINATIONAL USE OF DIFFERENT METHODS 129
6.1 TACTICS TO SELECT METHODS 129
6.1.1
13
C NMR METHODS 130
6.1.2 OR AND ORD 131
6.1.3 MATRIX 132
6.1.4 ECD 132
6.1.5 VCD METHOD 133
6.2 EXAMPLES AND DISCUSSION 133
6.3 REVISED STRUCTURES 138
6.3.1 ORD METHOD 139
6.3.2 COMBINATIONAL USE OF OR AND ECD 144
6.3.3 VCD AND ECD 146
6.3.4 COMPREHENSIVE USE OF OR, ECD, AND VCD 147
REFERENCES 160
PART III REACTIONS 163
7 ENANTIOSELECTIVE REACTION 165
7.1 ENANTIOSELECTIVE ADDITION 165
7.1.1 ORGANIC ZN- OR ZN-TI REAGENT 165
7.1.2 ORGANIC CU - ZN, CU - LI REAGENT 169
7.1.3 ORGANO-FE COMPLEXES 173
7.1.4 OTHER ORGANO-METALLIC COMPLEXES 175
7.1.5 ORGANO-SI REAGENTS 178
12 ENANTIOSELECTIVE REDUCTION 178
7.2.1 GREEN CHEMISTRY 181
7.3 ENANTIOSELECTIVE OXIDATION 184
7.4 PREDICTION OF EE USING CALCULATIONS 185
7.5 CATALYST TYPES 189
7.5.1 AMINO ALCOHOLS 189
7.5.2 CHIRAL LIGANDS CONTAINING N-O GROUP 190
7.5.3 CHIRAL AXIAL CATALYSTS 191
7.5.4 SOLID-SUPPORTED CHIRAL COMPOUNDS 192
7.5.5 SPIRAL CHIRAL COMPOUNDS 193
7.5.6 ASYMMETRIC-AXLE-SUPPORTED CHIRAL CATALYST 194
7.5.7 CHIRAL SHIFF-BASE LIGANDS 195
7.5.8 SOME ASYMMETRIC LEWIS ACIDS 196
7.5.9 ORGANIC P-CONTAINING LIGANDS 197
7.6 THREE PHENOMENA 198
7.6.1 CHIRALITY AMPLIFICATION (NONLINEAR EFFECT) 198
7.6.2 AUTO-SELF CATALYSIS 199
VIII
| CONTENTS
7.6.3 ODD - EVEN CARBON EFFECT 199
REFERENCES 201
8 CHEMOSELECTIVE REACTION 205
8.1 CHEMOSELECTIVE ADDITIONS 205
8.1.1 ADDITION TO C=0 OR C=C GROUPS
8.2 CHEMOSELECTIVE REDUCTION 210
8.3 CHEMOSELECTIVE OXIDATION 225
8.4 OTHER CHEMOSELECTIVE REACTIONS
REFERENCES 237
9 STEREOSELECTIVE REACTION 241
9.1 CONFORMATIONAL STUDY 241
9.2 EFFECT OF CONFORMATION ON REACTIONS 247
9.3 REGIOSELECTIVE REACTIONS 251
9.4 DIASTEREOSELECTIVE REACTIONS 260
9.4.1 DIASTEREOSELECTIVE ADDITIONS 260
9.4.2 OTHER DIASTEREOSELECTIVE REACTIONS 270
9.5 CALCULATION USING THEORETICAL PROTOCOL 272
REFERENCES 277
10 TOTAL ORGANIC SYNTHESIS 279
10.1 INTRODUCTION 279
10.2 RETROSYNTHESIS STRATEGIES 279
10.3 EXAMPLES IN SYNTHESIS 285
10.3.1 (+)-HIRSUTENE 285
10.3.2 (2R,3S)-RUBIGINONE A
2
AND ITS ANALOG 287
10.3.3 (+)-BREFELDIN A 290
10.3.4 MALYNGAMIDE U AND ITS AC REASSIGNMENT 292
10.3.5 TAXOL DERIVATIVES 296
10.3.6 AMPHIDINOLIDE T2 AND ITS DERIVATIVES 298
10.3.7 (+)-VINDOLINE 303
10.4 CALCULATION IN TOTAL SYNTHESIS 306
REFERENCES 309
205
231
INDEX 313 |
| any_adam_object | 1 |
| author | Zhu, Hua-Jie |
| author_GND | (DE-588)1073554651 |
| author_facet | Zhu, Hua-Jie |
| author_role | aut |
| author_sort | Zhu, Hua-Jie |
| author_variant | h j z hjz |
| building | Verbundindex |
| bvnumber | BV042697750 |
| classification_rvk | VK 5800 |
| ctrlnum | (OCoLC)901532103 (DE-599)DNB1065330804 |
| dewey-full | 547.1223 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.1223 |
| dewey-search | 547.1223 |
| dewey-sort | 3547.1223 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| indexdate | 2024-09-10T01:48:20Z |
| institution | BVB |
| isbn | 9783527338221 9783527688166 |
| language | English |
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| physical | XV, 318 Seiten Illustrationen, Diagramme |
| publishDate | 2015 |
| publishDateSearch | 2015 |
| publishDateSort | 2015 |
| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spelling | Zhu, Hua-Jie Verfasser (DE-588)1073554651 aut Organic stereochemistry experimental and computational methods Hua-Jie Zhu Weinheim Wiley-VCH Verlag GmbH & Co. KGaA [2015] © 2015 XV, 318 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Stereochemie (DE-588)4129569-9 gnd rswk-swf Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Organische Chemie Spektroskopie Stereochemie Stereochemie (DE-588)4129569-9 s Organische Verbindungen (DE-588)4043816-8 s 1\p DE-604 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-68817-3 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-68818-0 Erscheint auch als Online-Ausgabe, PDF 978-3-527-68815-9 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=5132962&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=028129309&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Zhu, Hua-Jie Organic stereochemistry experimental and computational methods Stereochemie (DE-588)4129569-9 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
| subject_GND | (DE-588)4129569-9 (DE-588)4043816-8 |
| title | Organic stereochemistry experimental and computational methods |
| title_auth | Organic stereochemistry experimental and computational methods |
| title_exact_search | Organic stereochemistry experimental and computational methods |
| title_full | Organic stereochemistry experimental and computational methods Hua-Jie Zhu |
| title_fullStr | Organic stereochemistry experimental and computational methods Hua-Jie Zhu |
| title_full_unstemmed | Organic stereochemistry experimental and computational methods Hua-Jie Zhu |
| title_short | Organic stereochemistry |
| title_sort | organic stereochemistry experimental and computational methods |
| title_sub | experimental and computational methods |
| topic | Stereochemie (DE-588)4129569-9 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
| topic_facet | Stereochemie Organische Verbindungen |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=5132962&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=028129309&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT zhuhuajie organicstereochemistryexperimentalandcomputationalmethods |