Stereochemistry and stereoselective synthesis: an introduction
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| Other Authors: | , , , , |
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH Verlag GmbH & Co. KGaA
[2016]
|
| Subjects: | |
| Online Access: | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33901-3/ Inhaltsverzeichnis |
| Physical Description: | XIV, 265 Seiten Illustrationen, Diagramme (teilweise farbig) |
| ISBN: | 9783527339013 |
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MARC
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| 245 | 1 | 0 | |a Stereochemistry and stereoselective synthesis |b an introduction |c edited by László Poppe, Mihály Nógrádi ; contributing authors László Poppe, József Nagy, Gábor Hornyánszky, Zoltán Boros |
| 264 | 1 | |a Weinheim |b Wiley-VCH Verlag GmbH & Co. KGaA |c [2016] | |
| 264 | 4 | |c © 2016 | |
| 300 | |a XIV, 265 Seiten |b Illustrationen, Diagramme (teilweise farbig) | ||
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| 653 | |a Biochemie | ||
| 653 | |a Biochemistry | ||
| 653 | |a Biowissenschaften | ||
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Life Sciences | ||
| 653 | |a Organic Chemistry | ||
| 653 | |a Organische Chemie | ||
| 653 | |a Pharmaceutical & Medicinal Chemistry | ||
| 653 | |a Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a Spectroscopy | ||
| 653 | |a Spektroskopie | ||
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| adam_text | CONTENTS
I
1.1
1.2
1.3
1.4
2
2.1
2.2
2
.
2.1
2
.
2.2
2.2.3
2.3
2.3.1
2.3.2
2.3.3
2.3.4
2.3.5
2.4
2.4.1
2.4.2
2.4.3
2.4.4
ABOUT THE COMPANION WEBSITE XI
INTRODUCTION XIII
PART I BASIC CONCEPTS AT THE MOLECULAR LEVEL
1
STRUCTURE AND PROPERTIES 3
THE COVALENT BOND AND THE OCTET RULE 3
REPRESENTATION OF CHEMICAL STRUCTURES 6
DESCRIPTION OF CHEMICAL STRUCTURE 8
PROBLEMS OF CORRELATING CHEMICAL STRUCTURE WITH PROPERTIES 10
REFERENCES 16
CONCEPTS OF STEREOCHEMISTRY
17
ELEMENTS AND GROUPS OF SYMMETRY 17
CLASSIFICATION OF THE BASIC CONCEPTS OF STEREOCHEMISTRY 21
CONCEPTS RELATED TO A SINGLE OBJECT (MOLECULE) OR PARTS OF
THEREOF 23
CONCEPTS REFERRING TO THE RELATIONSHIP OF TWO OBJECTS (MOLECULES)
(ISOMERISM, ISOMERIC RELATIONSHIP) 25
CONCEPTS REFERRING TO THE RELATIONSHIP OF PARTS OF AN OBJECT
(MOLECULE) OR MODES OF APPROACH TO AN OBJECT (TOPICITY) 31
STEREODESCRIPTORS 37
THE
D/L
SYSTEM, FISCHER*S PROJECTION 39
THE
R/S SYSTEM 41
HINDERED ROTATION AROUND A DOUBLE BOND,
E/Z ISOMERISM 43
AXIAL CHIRALITY, HELICITY,
M/P DESCRIPTORS 44
PLANAR CHIRALITY, RP /SP -DESCRIPTORS 46
PROSTEREOGENIC ELEMENTS, PROCHIRALITY 48
PROSTEREOISOMERISM AND PROCHIRALITY 48
DISTINCTION OF STEREOHETEROTOPIC GROUPS, THE
PRO-R/PRO-S
NOTATION 50
PROCHIRAL AND MESO COMPOUNDS, CENTER OF PSEUDOASYMMETRY 52
DISTINGUISHING OF STEREOHETEROTOPIC FACES, THE
RE/SI NOTATION 54
REFERENCES 56
PROBLEMS TO CHAPTERS 1 AND 2 57
3
3.1
3.2
3.3
4
4.1
4.2
4.2.1
4.2.2
4.2.3
4.2.4
4.2.5
5
5.1
5.2
5.2.1
5.2.2
5.2.3
5.3
5.3.1
5.3.2
5.3.2.1
5.3.2.2
5.4
PART II PROPERTIES AT THE LEVEL OF MATERIAL ASSEMBLIES 65
TIMESCALE, CONFORMATIONAL CHANGES 67
CONFORMATIONAL MOTION OF ETHANE AND ITS OPTICAL INACTIVITY 67
CONFORMATIONS AND OPTICAL INACTIVITY OF -BUTANE AND
1,2-DICHLOROETHANE 70
BIPHENYL AND SUBSTITUTED BIPHENYLS, ATROPISOMERISM 71
REFERENCES 74
ABSOLUTE CONFIGURATION 75
METHODS TO DETERMINE ABSOLUTE CONFIGURATION 78
STRATEGIES TO DETERMINE ABSOLUTE CONFIGURATION BY CHEMICAL
CORRELATION 79
TRANSFORMATIONS OF THE LIGANDS ATTACHED TO AN ASYMMETRIC UNIT
WITHOUT INFLUENCING THE BONDS BETWEEN THE ASYMMETRIC UNIT AND
THE LIGANDS 81
DEGRADATION OF MULTIPLE ASYMMETRIC UNITS OF A MORE COMPLEX
MOLECULE UNTIL ONLY ONE REMAINS INTACT 81
STEREOCONSTRUCTIVE STRATEGY THAT ADDS FURTHER ASYMMETRIC ELEMENTS
TO ONE OF THE KNOWN ABSOLUTE CONFIGURATION WITHOUT INFLUENCING
THE BONDS BETWEEN ITS ASYMMETRIC UNIT AND LIGANDS
82
SYMMETRIZATION OF ONE OR MORE ASYMMETRIC UNITS LEADING TO A
COMMON COMPOUND WITH LESS (BUT MORE THAN ONE) ASYMMETRIC
ELEMENTS 82
TRANSFORMATIONS INVOLVING STEREOSPECIFIC REACTIONS OF KNOWN
STEREOCHEMISTRY INFLUENCING THE BONDS BETWEEN THE ASYMMETRIC
UNIT AND THE LIGANDS 83
REFERENCES 84
METHODS FOR THE DETERMINATION OF ENANTIOMERIC COMPOSITION 87
CHIROPTICAL METHODS 89
NMR METHODS BASED ON DIASTEREOTOPICITY 89
METHODS BASED ON FORMING DIASTEREOMERIC DERIVATIVES 89
NMR METHODS BASED ON THE USE OF CHIRAL SOLVENTS (SOLVATING
AGENTS)
92
NMR METHODS BASED ON CHIRAL SHIFT REAGENTS 93
CHROMATOGRAPHIC AND RELATED METHODS BASED ON DIASTEREOMERIC
INTERACTIONS 94
SEPARATION ON A DIASTEREOSELECTIVE (ACHIRAL) STATIONARY PHASE 94
USE OF AN ENANTIOSELECTIVE (CHIRAL) STATIONARY PHASE 96
GAS CHROMATOGRAPHY 97
HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY 98
KINETIC METHODS BASED ON ENANTIOMER SELECTIVITY 99
5.4.1 ENZYMATIC METHODS 100
5.4.2 NONENZYMATIC (CHEMICAL) METHODS 101
5.5 FUSION METHODS 102
5.6 METHODS BASED ON ISOTOPE DILUTION 102
5.7 POTENTIOMETRIE METHODS 102
REFERENCES 103
6 TAUTOMERISM 105
6.1 TYPES OF TAUTOMERISM 106
6.1.1 VALENCE TAUTOMERISM I06
6.1.2 CLASSIC TAUTOMERISM 107
6.2 PROTOTROPY 108
6.2.1 OXO-ENOL TAUTOMERISM I0 5
6.2.2 IMINE-ENAMINE TAUTOMERISM 110
6.2.3 AMIDE-IMIDO ACID AND RELATED TAUTOMERISMS UE 2
6.2.4 TAUTOMERISM OF ALIPHATIC NITRO COMPOUNDS 113
6.2.5 TAUTOMERISM OF CARBONIC ACID DERIVATIVES CONTAINING CUMULATED
DOUBLE BONDS 113
6.2.6 RING-CHAIN TAUTOMERISM UE 4
6.3 METHODS FOR STUDYING TAUTOMERISM 115
6.4 NITROGEN INVERSION 115
REFERENCES UE 6
PROBLEMS TO PART II 117
PART III GENERAL CHARACTERISTICS OF STEREOSELECTIVE REACTIONS 125
1 TYPES AND CLASSIFICATION OF SELECTIVITIES 127
7.1 MAIN TYPES OF SELECTIVITY 127
7.1.1 SUBSTRATE SELECTIVITY 127
7.1.2 PRODUCT SELECTIVITY 127
7.2 CLASSIFICATION OF SELECTIVITIES 128
7.2.1 CHEMOSELECTIVITY 130
7.2.1.1 INTERPRETATION OF CHEMOSELECTIVITY 130
7.2.1.2 CHEMOSELECTIVITY IN BIOCATALYSIS 131
7.2.2 REGIOSELECTIVITY 131
7.2.2.1 SUBSTRATE REGIOSELECTIVITY 132
7.2.2.2 PRODUCT REGIOSELECTIVITY 132
REFERENCES 135
8 STEREOSELECTIVE AND STEREOSPECIFIC REACTIONS 137
8.1 STEREOSPECIFICITY 137
8.2 STEREOSELECTIVITY 138
8.3 SELECTIVE SYNTHESES OF ENANTIOMERS 139
8.4 DIASTEREOMER SELECTIVITY 141
8.5 DIASTEREOTOPE SELECTIVITY 142
8.5.1 DIASTEREOTOPE SELECTIVITY WITH THE FORMATION OF A NEW CHIRAL
ELEMENT 143
8.5.2 CHIRAL AUXILIARY GROUPS 145
8.5.3 ENANTIODIVERGENT SYNTHETIC STRATEGY EMPLOYING CHIRAL AUXILIARY
GROUPS 146
8.5.4 SIGNIFICANCE OF SEPARATING THE DIASTEREOMERS FORMED 147
8.5.4.1 PURIFICATION OF ENANTIOMERS BY THE SEPARATION OF DIASTEREOMERS
FORMED WITH THE AID OF AN ACHIRAL BIDENTATE REAGENT 149
8.5.5 DIASTEREOTOPIC VERSION OF ASYMMETRIC TRANSFORMATION BY INDUCED
CRYSTALLIZATION (CLAT) INVOLVING DIASTEREOTOPIC INTERACTIONS 149
8.5.6 DIASTEREOTOPE SELECTIVITY IN BIOTRANSFORMATIONS 153
8.5.6.1 SELECTIVE BIOTRANSFORMATIONS OF DIASTEREOTOPIC GROUPS 153
8.5.6.2 SELECTIVE BIOTRANSFORMATION OF DIASTEREOTOPIC FACES 153
8.6 ENANTIOMER SELECTIVITY 154
8.6.1 DEGREE OF ENANTIOMER SELECTIVITY IN IRREVERSIBLE PROCESSES 155
8.6.2 KINETIC RESOLUTION USING CHEMICAL SYSTEMS 158
8.6.2.1 PARALLEL KINETIC RESOLUTION WITH CHEMICAL SYSTEMS 160
8.6.3 KINETIC RESOLUTION WITH BIOCATALYSTS 160
8.6.3.1 PARALLEL KINETIC RESOLUTION WITH BIOCATALYSIS 166
8.6.4 DYNAMIC KINETIC RESOLUTION (DKR) 166
8.6.4.1 DYNAMIC KINETIC RESOLUTION USING CHEMICAL SYSTEMS 167
8.6.4.2 DYNAMIC KINETIC RESOLUTIONS WITH BIOCATALYSIS 168
5.6.4.3 DYNAMIC KINETIC RESOLUTION (DKR) INVOLVING BASE-CATALYZED
RACEMIZATION 168
5.6.4.4 DKR INVOLVING ACID-CATALYZED RACEMIZATION 169
8.6.4.5 DKR COMBINED WITH RACEMIZATION BY RING OPENING 169
8.6.4.6 DKR INVOLVING METAL-CATALYZED RACEMIZATION 170
5.6.4.7 DYNAMIC KINETIC RESOLUTIONS UTILIZING OTHER CHEMICAL
RACEMIZATION PROCESSES 171
5.6.4.8 DYNAMIC KINETIC RESOLUTION COMPRISING BIOCATALYTIC
RACEMIZATION 171
8.6.5 CRYSTALLIZATION-INDUCED DYNAMIC RESOLUTION (CIDR) 172
8.6.6 KINETIC RESOLUTION FOLLOWED BY CONFIGURATIONAL INVERSION 174
8.7 ENANTIOTOPE SELECTIVITY 175
8.7.1 ENANTIOTOPE SELECTIVITY IN CHEMICAL SYSTEMS 177
8.7.2 ENANTIOTOPE SELECTIVITY IN BIOCATALYTIC SYSTEMS 179
8.7.2.1 TRANSFORMATIONS OF ENANTIOTOPIC GROUPS BY BIOCATALYSIS 179
8.7.3 CONSEQUENCES OF OPPOSING ENANTIOTOPE-SELECTIVE
TRANSFORMATIONS 182
8.7.4 KINETIC AMPLIFICATION 183
8.7.5 ENANTIODIVERGENT REACTIONS FOLLOWING THE TRANSFORMATION OF
ENANTIOTOPIC GROUPS 185
8.8 COMBINATION OF MORE THAN ONE TYPE OF SELECTIVITY 186
REFERENCES 187
PROBLEMS TO PART III 189
PART IV APPLICATIONS OF ENANTIOSELECTIVE METHODS 201
9 STOICHIOMETRIC METHODS OF ENANTIOSELECTIVE SYNTHESIS 203
9.1 DIASTEREOTOPE SELECTIVE METHODS 203
9.1.1 SUBSTRATE-CONTROLLED SELECTIVITY 203
9.1.2 DIASTEREOTOPE SELECTIVITY CONTROLLED BY AN AUXILIARY
GROUP-ENANTIOSELECTIVE SYNTHESIS 204
9.1.3 DOUBLE ASYMMETRIC INDUCTION. CONCERTED DIASTEREOTOPE SELECTIVITY
OF CHIRAL MOLECULES 208
9.2 ENANTIOTOPE SELECTIVE METHODS 211
9.2.1 REAGENT-CONTROLLED SELECTIVITY 211
10 CATALYTIC METHODS OF ENANTIOSELECTIVE SYNTHESIS 213
10.1 CHEMICAL CATALYSIS 213
10.1.1 CHIRAL (ASYMMETRIC) CATALYTIC HYDROGENATION 213
10.1.2 ENANTIOTOPE-SELECTIVE CATALYTIC EPOXIDATION 219
10.1.3 STEREOSELECTIVE CATALYTIC DIOL FORMATION 228
10.1.4 FORMATION OF A C -C BOND BY CHIRAL CATALYSIS 229
10.1.5 STEREOSELECTIVE CATALYTIC MICHAEL ADDITIONS 232
10.1.6 CATALYTIC STEREOSELECTIVE NUCLEOPHILIC ADDITION ONTO A CARBONYL
GROUP 234
10.1.7 DOUBLE-ENANTIOTOPE-SELECTIVE CATALYTIC ALDOL REACTIONS 238
10.1.8 ENANTIOTOPE-SELECTIVE CATALYTIC
SIMMONS-SMITH REACTION
(CYCLOPROPANATION) 239
10.1.9 STEREOSELECTIVE CATALYTIC DIELS-ALDER REACTION 240
10.2 BIOCATALYSIS 244
10.2.1 SUBSTRATE SELECTIVITY (ENANTIOMER SELECTIVITY) - KINETIC
RESOLUTION 246
10.2.2 SUBSTRATE SELECTIVITY (ENANTIOMER SELECTIVITY) - DYNAMIC KINETIC
RESOLUTION 249
10.2.3 ENANTIOTOPE-SELECTIVE BIOTRANSFORMATIONS 251
10.2.3.1 OXIDOREDUCTASES 251
10.2.3.2 LYASES 253
INDEX
257
|
| any_adam_object | 1 |
| author2 | Poppe, László 1959- Poppe, László 1959- Nógrádi, Mihály 1933- Nógrádi, Mihály 1933- Nagy, József Hornyánszky, Gábor 1968- Boros, Zoltán |
| author2_role | edt ctb edt ctb ctb ctb ctb |
| author2_variant | l p lp l p lp m n mn m n mn j n jn g h gh z b zb |
| author_GND | (DE-588)1116972247 (DE-588)1116977982 (DE-588)1116978822 (DE-588)1116979284 (DE-588)111697973X |
| author_facet | Poppe, László 1959- Poppe, László 1959- Nógrádi, Mihály 1933- Nógrádi, Mihály 1933- Nagy, József Hornyánszky, Gábor 1968- Boros, Zoltán |
| building | Verbundindex |
| bvnumber | BV043354705 |
| classification_rvk | VK 5800 VK 5801 |
| ctrlnum | (OCoLC)958159796 (DE-599)DNB1081678631 |
| dewey-full | 540 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences |
| dewey-raw | 540 |
| dewey-search | 540 |
| dewey-sort | 3540 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| id | DE-604.BV043354705 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T07:23:48Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527339013 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-028774099 |
| oclc_num | 958159796 |
| open_access_boolean | |
| owner | DE-20 DE-29T DE-703 DE-11 DE-19 DE-BY-UBM DE-634 DE-83 |
| owner_facet | DE-20 DE-29T DE-703 DE-11 DE-19 DE-BY-UBM DE-634 DE-83 |
| physical | XIV, 265 Seiten Illustrationen, Diagramme (teilweise farbig) |
| publishDate | 2016 |
| publishDateSearch | 2016 |
| publishDateSort | 2016 |
| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spelling | Stereochemistry and stereoselective synthesis an introduction edited by László Poppe, Mihály Nógrádi ; contributing authors László Poppe, József Nagy, Gábor Hornyánszky, Zoltán Boros Weinheim Wiley-VCH Verlag GmbH & Co. KGaA [2016] © 2016 XIV, 265 Seiten Illustrationen, Diagramme (teilweise farbig) txt rdacontent n rdamedia nc rdacarrier Stereoselektive Synthese (DE-588)4135601-9 gnd rswk-swf Stereochemie (DE-588)4129569-9 gnd rswk-swf Biochemie Biochemistry Biowissenschaften Chemie Chemistry Life Sciences Organic Chemistry Organische Chemie Pharmaceutical & Medicinal Chemistry Pharmazeutische u. Medizinische Chemie Spectroscopy Spektroskopie Stereochemie (DE-588)4129569-9 s Stereoselektive Synthese (DE-588)4135601-9 s DE-604 Poppe, László 1959- (DE-588)1116972247 edt ctb Nógrádi, Mihály 1933- (DE-588)1116977982 edt ctb Nagy, József (DE-588)1116978822 ctb Hornyánszky, Gábor 1968- (DE-588)1116979284 ctb Boros, Zoltán (DE-588)111697973X ctb Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-69630-7 Erscheint auch als Online-Ausgabe, ePub 978-3-527-69631-4 Erscheint auch als Online-Ausgabe, Mobi 978-3-527-69632-1 Erscheint auch als Online-Ausgabe, oBook 978-3-527-34117-7 http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33901-3/ Verlag DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028774099&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Stereochemistry and stereoselective synthesis an introduction Stereoselektive Synthese (DE-588)4135601-9 gnd Stereochemie (DE-588)4129569-9 gnd |
| subject_GND | (DE-588)4135601-9 (DE-588)4129569-9 |
| title | Stereochemistry and stereoselective synthesis an introduction |
| title_auth | Stereochemistry and stereoselective synthesis an introduction |
| title_exact_search | Stereochemistry and stereoselective synthesis an introduction |
| title_full | Stereochemistry and stereoselective synthesis an introduction edited by László Poppe, Mihály Nógrádi ; contributing authors László Poppe, József Nagy, Gábor Hornyánszky, Zoltán Boros |
| title_fullStr | Stereochemistry and stereoselective synthesis an introduction edited by László Poppe, Mihály Nógrádi ; contributing authors László Poppe, József Nagy, Gábor Hornyánszky, Zoltán Boros |
| title_full_unstemmed | Stereochemistry and stereoselective synthesis an introduction edited by László Poppe, Mihály Nógrádi ; contributing authors László Poppe, József Nagy, Gábor Hornyánszky, Zoltán Boros |
| title_short | Stereochemistry and stereoselective synthesis |
| title_sort | stereochemistry and stereoselective synthesis an introduction |
| title_sub | an introduction |
| topic | Stereoselektive Synthese (DE-588)4135601-9 gnd Stereochemie (DE-588)4129569-9 gnd |
| topic_facet | Stereoselektive Synthese Stereochemie |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33901-3/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028774099&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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