Stereoselective synthesis: a practical approach
Saved in:
| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim u.a.
VCH
1995
|
| Edition: | 2., thoroughly rev. and updated ed. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Literaturverz. S. [315] - 346 |
| Physical Description: | XVIII, 368 S. graph. Darst. |
| ISBN: | 3527292438 352729242X 1560818956 |
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Record in the Search Index
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| adam_text | MIHAELY NOEGRAEDI STEREOSELECTIVE SYNTHESIS A PRACTICAL APPROACH FOREWORD
BY A. I. MEYERS SECOND, THOROUGHLY REVISED AND UPDATED EDITION WEINHEIM
* NEW YORK BASEL * CAMBRIDGE * TOKYO VCH CONTENTS LIST OF SYMBOLS AND
ABBREVIATIONS XV INTRODUCTION XVII 1 GENERAL CONCEPTS OF STEREOSELECTIVE
SYNTHESIS 1 1.1 PRINCIPLES OF DIFFERENTIATING MOLECULES 1 1.2
CHARACTERIZATION OF STEREOISOMERS. CONFORMATION AND CONFIGURATION 4 1.3
INTRAMOLECULAR SYMMETRY. TOPICITY AND PROCHIRALITY 7 1.4 SELECTIVITY IN
CHEMISTRY 11 1.4.1 SUBSTRATE SELECTIVITY 11 1.4.1.1 SUBSTRATE
DIASTEREOSELECTIVITY (DIASTEREOMER SELECTIVITY) 12 1.4.1.2 SUBSTRATE
ENANTIOSELECTIVITY (ENANTIOMER SELECTIVITY). KINETIC RESOLU- TION 13
1.4.2 PRODUCT SELECTIVITY 17 1.4.2.1 FORMATION OF STEREOISOMERS 18
1.4.2.2 CONDITIONS NECESSARY FOR STEREOSELECTIVITY 23 1.4.2.3 CONCEPT OF
STEREODIFFERENTIATION 27 1.4.2.4 METHODS FOR INDUCING STEREOSELECTIVITY
27 1.4.3 STEREOSELECTIVE SYNTHETIC STRATEGIES 36 1.4.3.1
ENANTIOCONVERGENT SYNTHESIS 36 1.4.3.2 SELECTIVE PREPARATION OF BOTH
ENANTIOMERS FROM A SINGLE SUBSTRATE 39 1.5 KINETICS AND THERMODYNAMICS
OF STEREOSELECTIVE REACTIONS 41 2 STEREOSELECTIVE CATALYTIC REDUCTIONS
45 2.1 STEREOSELECTIVE HOMOGENEOUS HYDROGENATIONS WITH RHODIUM-,
RUTHENIUM- AND IRIDIUM-PHOSPHINE CATALYSTS 45 2.1.1 HYDROGENATION OF
OLEFINIC BONDS 48 2.1.1.1 CHIRAL PHOSPHORUS CONTAINING LIGANDS 48 2.1.2
ENANTIOSELECTIVE CATALYTIC HYDROGENATION OF KETONES AND IMINES 66 2.1.3
DIASTEREOSELECTIVE HYDROGENATIONS IN HOMOGENEOUS PHASE 68 2.2 CATALYTIC
HYDROSILYLATION 70 CONTENTS 2.3 HETEROGENEOUS STEREOSELECTIVE CATALYTIC
HYDROGENATIONS 76 2.3.1 ENANTIOSELECTIVE HETEROGENEOUS CATALYTIC
HYDROGENATIONS 77 2.3.2 DIASTEREOSELECTIVE HETEROGENEOUS CATALYTIC
HYDROGENATIONS 78 3 STEREOSELECTIVE NON-CATALYTIC REDUCTIONS 81 3.1
ENANTIOSELECTIVE REDUCTIONS 81 3.1.1 CHIRAL LITHIUM ALUMINUM HYDRIDES 81
3.1.1.1 REDUCTION OF CARBONYL GROUPS 81 3.1.1.2 REDUCTION OF C = N AND
C=C BONDS 88 3.1.2 CHIRALLY MODIFIED HYDRIDOBORATES 88 3.1.3 CHIRAL
BORANES AND BORONATES 90 3.1.4 ENANTIOSELECTIVE REDUCTIONS WITH HYDRIDE
TRANSFER FROM CARBON 92 3.1.4.1 CHIRAL TRIALKYLBORANES 92 3.1.4.2 CHIRAL
METAL ALKYLS 94 3.1.4.3 CHIRAL METAL ALKOXIDES 95 3.1.4.4 CHIRAL
1,4-DIHYDROPYRIDINES 95 3.1.5 CORRELATION OF SUBSTRATE CONSTITUTION AND
ENANTIOSELECTIVITY 96 3.2 DIASTEREOSELECTIVE REDUCTIONS OF CARBONYL
GROUPS 100 3.2.1 STEREOCHEMISTRY OF DIASTEREOSELECTIVE KETONE REDUCTIONS
101 3.2.2 PRACTICAL ASPECTS OF DIASTEREOSELECTIVE KETONE REDUCTIONS 110
4 STEREOSELECTIVE OXIDATIONS 123 4.1 ENANTIOSELECTIVE OXIDATIONS 123
4.1.1 EPOXIDATION WITH CHIRAL OXIDANTS 123 4.1.2 OXIDATIONS IN THE
PRESENCE OF CHIRAL CATALYSTS 124 4.2 DIASTEREOSELECTIVE OXIDATIONS 130
4.2.1 DIASTEREOSELECTIVE EPOXIDATION 130 4.2.2 VARIOUS
DIASTEREOSELECTIVE OXIDATIONS 133 5 STEREOSELECTIVE CARBON-CARBON BOND
FORMING REACTIONS BY NUCLEOPHILIC ADDITION TO CARBONYL GROUPS 135 5.1
ADDITION OF SIMPLE NUCLEOPHILES TO CARBONYL COMPOUNDS 136 5.1.1
ENANTIOSELECTIVE ADDITIONS 136 5.1.2 DIASTEREOSELECTIVE ADDITIONS 139
5.1.3 ADDITIONS TO C = N BONDS 154 5.2 ADDITIONS INVOLVING ALLYLMETAL
AND ALLYLBORON COMPOUNDS 157 5.2.1 GENERAL ASPECTS OF ALLYLMETAL
ADDITION 157 5.2.2 ADDITION OF ALLYLBORON COMPOUNDS 162 CONTENTS XIII
5.2.3 ADDITION OF ALLYLTITANIUM COMPOUNDS 167 5.2.4 ADDITION OF
ALLYLSILANES 170 5.2.5 ADDITION OF ALLYLSTANNANES 173 5.2.6 ADDITION OF
OTHER ALLYLMETALS 175 5.3 STEREOSELECTIVE ALDOL REACTIONS 177 5.3.1
STEREOCHEMISTRY AND MECHANISM OF THE ALDOL REACTION 178 5.3.2 GENERATION
OF ENOLATES AND THEIR ADDITION TO ACHIRAL ALDEHYDES AND KETONES 184
5.3.3 ADDITION OF ENOLATES TO KETONES (THE CROSS-ALDOL REACTION) 197
5.3.4 ADDITION OF ACHIRAL ENOLATES TO ACHIRAL ALDEHYDES UNDER CHIRAL
CATALYSIS 198 5.3.5 ADDITION OF CHIRAL ENOLATES TO ACHIRAL ALDEHYDES 200
5.3.6 ADDITION OF ACHIRAL ENOLATES TO CHIRAL ALDEHYDES 205 5.3.7
STEREOSELECTIVE ALDOL CONDENSATIONS 209 5.4 CATALYTIC ADDITION OF
ISONITRILES TO ALDEHYDES 210 6 STEREOSELECTIVE CARBON-CARBON BOND
FORMING REACTIONS 213 6.1 CARBON-CARBON BOND FORMATION INVOLVING OLEFINS
213 6.1.1 ADDITION OF CARBANIONS TO ACTIVATED OLEFINS 213 6.1.1.1 THE
MICHAEL ADDITION 213 6.1.1.2 ADDITION OF METALORGANICS TO
A,/MJNSATURATED KETONES AND ESTERS 218 6.1.1.3 ADDITION OF METALORGANICS
TO A,/MJNSATURATED AZOMETHINES AND 2-VINYLOXAZOLINES 224 6.1.2 ALLYLIC
ALKYLATION 226 6.1.3 STEREOSELECTIVE HYDROCARBONYLATION 229 6.2
STEREOSELECTIVE ALKYLATIONS 230 6.2.1 ALKYLATION OF ENOLATES 230 6.2.1.1
ALKYLATION OF ENOLATES WITH A REMOVABLE CHIRAL AUXILIARY GROUP 231
6.2.1.2 DIASTEREOSELECTIVE ALKYLATION OF ENOLATES 240 6.2.2 ALKYLATION
OF STABILIZED CARBANIONS 241 6.2.3 ALKYLATION OF ENAMINES AND METALLATED
AZOMETHINES 244 6.2.4 ALKYLATION OF METALLATED HYDRAZONES AND AMIDINES
246 6.3 ENANTIOSELECTIVE GRIGNARD CROSS-COUPLING AND OTHER
STEREOSELECTIVE CATALYTIC CARBON-CARBON BOND FORMING REACTIONS 249 6.3.1
GRIGNARD CROSS-COUPLING 249 6.3.2 STEREOSELECTIVE CODIMERIZATION OF
OLEFINS 251 6.4 MISCELLANEOUS STEREOSELECTIVE CARBON-CARBON BOND FORMING
REACTIONS 252 XIV CONTENTS 7 STEREOSELECTIVE CARBON-CARBON BOND
FORMATION BY PERICYCLIC REAC- TIONS 257 7.1 ASYMMETRIE INDUCTION IN
CYCLOADDITIONS 257 7.1.1 ASYMMETRIE INDUCTION IN THE DIELS-ALDER
REACTION 258 7.1.2 ASYMMETRIE INDUCTION IN [3 + 2] CYCLOADDITIONS 268
7.1.3 ASYMMETRIE INDUCTION IN [2 + 2] CYCLOADDITIONS 269 7.1.4
STEREOSELECTIVE CARBENE ADDITIONS 273 7.2 CHIRALITY TRANSFER IN
SIGMATROPIC REARRANGEMENTS 277 7.2.1 [3,3] SIGMATROPIC REARRANGEMENTS
278 7.2.2 [2,3] SIGMATROPIC REARRANGEMENTS 283 7.2.3 ENE REACTIONS 287
STEREOSELECTIVE FORMATION OF CARBON-HETEROATOM BONDS 293 .1
STEREOSELECTIVE FORMATION OF CARBON-NITROGEN BONDS 293 .2
STEREOSELECTIVE FORMATION OF CARBON-PHOSPHORUS BONDS 296 .3
STEREOSELECTIVE FORMATION OF CARBON-OXYGEN BONDS 297 .4 STEREOSELECTIVE
FORMATION OF CARBON-SULFUR BONDS 303 .5 STEREOSELECTIVE FORMATION OF
CARBON-HALOGEN BONDS 305 .6 STEREOSELECTIVE PROTONATION AND HYDROGEN
MIGRATION 306 APPENDIX 311 REFERENCES 315 GENERAL REFERENCES 357 SUBJECT
INDEX 359
|
| any_adam_object | 1 |
| author | Nógrádi, Mihály |
| author_facet | Nógrádi, Mihály |
| author_role | aut |
| author_sort | Nógrádi, Mihály |
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| discipline | Chemie / Pharmazie Chemie |
| edition | 2., thoroughly rev. and updated ed. |
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| illustrated | Illustrated |
| indexdate | 2024-07-09T17:40:55Z |
| institution | BVB |
| isbn | 3527292438 352729242X 1560818956 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-006477443 |
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| owner | DE-355 DE-BY-UBR DE-29T DE-91G DE-BY-TUM DE-703 DE-20 DE-19 DE-BY-UBM DE-634 DE-83 DE-188 |
| owner_facet | DE-355 DE-BY-UBR DE-29T DE-91G DE-BY-TUM DE-703 DE-20 DE-19 DE-BY-UBM DE-634 DE-83 DE-188 |
| physical | XVIII, 368 S. graph. Darst. |
| publishDate | 1995 |
| publishDateSearch | 1995 |
| publishDateSort | 1995 |
| publisher | VCH |
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| spelling | Nógrádi, Mihály Verfasser aut Stereoselective synthesis a practical approach Mihály Nógrádi 2., thoroughly rev. and updated ed. Weinheim u.a. VCH 1995 XVIII, 368 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Literaturverz. S. [315] - 346 Stereoselektive Synthese (DE-588)4135601-9 gnd rswk-swf Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Stereoselektive Synthese (DE-588)4135601-9 s Organische Verbindungen (DE-588)4043816-8 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006477443&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Nógrádi, Mihály Stereoselective synthesis a practical approach Stereoselektive Synthese (DE-588)4135601-9 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
| subject_GND | (DE-588)4135601-9 (DE-588)4043816-8 |
| title | Stereoselective synthesis a practical approach |
| title_auth | Stereoselective synthesis a practical approach |
| title_exact_search | Stereoselective synthesis a practical approach |
| title_full | Stereoselective synthesis a practical approach Mihály Nógrádi |
| title_fullStr | Stereoselective synthesis a practical approach Mihály Nógrádi |
| title_full_unstemmed | Stereoselective synthesis a practical approach Mihály Nógrádi |
| title_short | Stereoselective synthesis |
| title_sort | stereoselective synthesis a practical approach |
| title_sub | a practical approach |
| topic | Stereoselektive Synthese (DE-588)4135601-9 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
| topic_facet | Stereoselektive Synthese Organische Verbindungen |
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