Aziridines and epoxides in organic synthesis:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
WILEY-VCH
2006
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXI, 492 S. graph. Darst. 240 mm x 170 mm |
| ISBN: | 3527312137 9783527312139 |
Internformat
MARC
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| 245 | 1 | 0 | |a Aziridines and epoxides in organic synthesis |c ed. by Andrei K. Yudin |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2006 | |
| 300 | |a XXI, 492 S. |b graph. Darst. |c 240 mm x 170 mm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Composés organiques - Synthèse | |
| 650 | 4 | |a Époxydes | |
| 650 | 4 | |a Aziridines | |
| 650 | 4 | |a Epoxy compounds | |
| 650 | 4 | |a Organic compounds |x Synthesis | |
| 650 | 0 | 7 | |a Aziridine |0 (DE-588)4143796-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Epoxide |0 (DE-588)4152561-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Organische Synthese |0 (DE-588)4075695-6 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Epoxide |0 (DE-588)4152561-9 |D s |
| 689 | 0 | 1 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 0 | |5 DE-604 | |
| 689 | 1 | 0 | |a Aziridine |0 (DE-588)4143796-2 |D s |
| 689 | 1 | 1 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 1 | |5 DE-604 | |
| 700 | 1 | |a Judin, Andrej K. |e Sonstige |4 oth | |
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| 999 | |a oai:aleph.bib-bvb.de:BVB01-014744957 | ||
Datensatz im Suchindex
| _version_ | 1804135273768943616 |
|---|---|
| adam_text | TABLE OF CONTENTS FOREWORD V11 PREFACE XVII LIST OF CONTRIBUTORS XIX
ASYMMETRIC SYNTHESIS OF EPOXIDES AND AZIRIDINES FIOM ALDEHYDES AND
IMINES 1 VARINDER K. AGGANVAL, D. MICHAEL BADINE, UND VIJAYALAKSHMI A.
MOORTHIE INTRODUCTION 1 ASYMMETRIC EPOXIDATION OF CARBONYL COMPOUNDS 1
ARYL, VINYL, AND ALKYL EPOXIDES 2 STOICHIOMETRIC YLIDE-MEDIATED
EPOXIDATION 2 CATALYTIC YLIDE-MEDIATED EPOXIDATION 3 DISCUSSION OF
FACTORS AFFECTING DIASTEREO- AND ENANTIOSELECTIVITY 8 TERMINAL EPOXIDES
10 EPOXY ESTERS, AMIDES, ACIDS, KETONES, AND SULFONES 11 SULFUR
YLIDE-MEDIATED EPOXIDATION 1 1 DARZENS REACTION 13 DARZENS REACTIONS IN
THE PRESENCE OF CHIRAL AUXILIARIES 13 DARZENS REACTIONS WITH CHIRAL
REAGENTS 18 DARZENS REACTIONS WITH CHIRAL CATALYSTS 20 ASYMMETRIC
AZIRIDINATION OF IMINES 22 AZIRIDINES BEARING ELEDRON-WITHDRAWING
GROUPS: ESTERS AND AMIDES 23 AZA-DARZENS ROUTE 23 REACTIONS BETWEEN
IMINES AND CARBENES 24 AZIRIDINES BY GUANIDINIUM YLIDE CHEMISTRY 27
AZIRIDINES BEARING ALKYL, ARYL, PROPARGYL, AND VINYL GROUPS 28 ARYL,
VINYL, AND ALKYL AZIRIDINES: STOICHIOMETRIC ASYMMETRIC YLIDE-MEDIATED
AZIRIDINATION 28 ARYL, VINYL, AND ALKYL AZIRIDINES: CATALYTIC ASYMMETRIC
YLIDE-MEDIATED AZIRIDINATION 31 SUMMARY AND OUTLOOK 33 REFERENCES 34
AZIRIDINES OND EPOXIDES IN ORGANIC SYNTHESIS. ANDREI K. YUDIN COPYRIGHT
0 2006 WILEY-VCH VERLAG GMBH & CO. KGAA, WEINHEIM ISBN: 3-527-31213-7 X
TABLE OFCONTENTS I VINYLAZIRIDINES IN ORGANIC SYNTHESIS 37 HIROAKI OHNO
LNTRODUCTION 37 DIRECI SYNTHESIS OF VINYLAZIRIDINES [I] 37 ADDITION OF
NITRENE TO DIENES 37 ADDITION OF ALLYLIC YLIDES AND RELATED REAGENTS TO
IMINES 39 CYDIZATION OF AMINO ALCOHOLS AND RELATED COMPOUNDS 42
CYDIZATION OF AMINO ALLENES 45 AZIRIDINATION OF A,SS-UNSATURATED OXIMES
AND HYDRAZONES 46 RING-OPENING REACTIONS WITH NUCLEOPHILES 47 HYDRIDE
REDUCTION 47 ORGANOCOPPER-MEDIATED ALKYLATION 48 REACIIONS WITH OXYGEN
NUCLEOPHILES 51 REACTIONS WITH OTHER NUCLEOPHILES 54 LSOMERIZATION
INCLUDING REARRANGEMENT 54 AZA-[3,3]-CLAISEN REARRANGEMENT 55 PYRROLINE
FORMATION 57 AZA-[L, 31-WITTIG REARRANGEMENT 60 HYDROGEN SHIFI 61
REARRANGEMENT WITH AN ARYL GROUP ON THE AZIRIDINE CARBON 62
EPIMERIZATION 63 CYDOADDITION 64 CYDOADDITIONS OF LSOCYANATES AND
RELATED COMPOUNDS 64 CARBONYLATIVE RING-EXPANSION TO LACTAMS 65 ELECTRON
TRANSFER TO VINYLAZIRIDINES 67 CONDUSIONS 68 REFERENCES 68 ASYMMETRIE
SYNTHESES WITH AZIRIDINECARBOXYLATE AND AZIRIDINE- PHOSPHONATE BUILDING
BLOCKS 73 PING ZHOU, BANG-CHI CHEN, AND FRANKLIN A. DAVIS LNTRODUCTION
73 PREPARATION OF AZIRIDINE-2-CARBOXYLATES AND AZIRIDINE-2-PHOSPHO-
NATES 74 PREPARATION OF AZIRIDINE -2-CARBOXYLATES 74 CYCLIZATION OF
HYDROXY AMINO ESTERS 74 CYCLIZATION OF HYDROXY AZIDO ESTERS 76
CYDIZATION OF A-HALO- AND A-SULFONYLOXY-SS-ARNINO ESTERS AND AMIDES 76
AZIRIDINATION OF A,SS-UNSATURATED ESTERS 77 AZIRIDINATION OF IMINES 79
AZIRIDINATION OF ALDEHYDES 82 2-CARBOXYLATION OF AZIRIDINES 83
RESOLUTION OF RACEMIC AZIRIDINE-2-CARBOXYLATES 84 PREPARATION OF
AZIRIDINE-2-PHOSPHONATES 85 TABLE OF CONTENTS I X REACTIONS OF
AZINDINE-2-CARBOXYLATES AND AZIRIDINE-2-PHOSPHO- NATES 87 REACTIONS OF
AZIRIDINE-2-CARBOXYLATES 87 REDUCTIVE RING-OPENING 88 BASE-PROMOTED
RING-OPENING 89 NUCLEOPHILIC RING-OPENING 89 ELECTROPHILIC SUBSTITUTIONS
AT THE C-2 CARBON ATOM 97 RING-EXPANSION REACTIONS 98 CONVERSION TO
AZIRINE-2-CARBOXYLATES 102 REACTIONS OF AZIRIDINE-2-PHOSPHONATES 103
APPLICATIONS IN NATURAL PRODUCT SYNTHESES 105 SUMMARY AND CONCLUSIONS 11
1 REFERENCES 11 2 SYNTHESIS OF AZIRIDINES 117 DEDICATED, WITH RESPECT,
TO PROFSSOR SIR CHARLES REES, FRS JOSEPH B. SWEENEY INTRODUCTION 117
OVEMIEW AND GENERAL FEATURES 11 7 ADDITION TO ALKENES 118 ADDITION OF
NITRENES AND NITRENOIDS TO ALKENES 119 AZIRIDINES BY
ADDITION-ELIMINATION PROCESSES 128 ADDITION TO IMINES 129 CARBENE
METHODOLOGY 129 AZA-DARZENS AND ANALOGOUS REACTIONS I32 ADDITION TO
AZIRINES 134 AZINDINES THROUGH CYCLIZATION 139 FROM EPOXIDES 139 FROM
1.2-AMINOALCOHOLS AND 1,2-AMINOHALIDES 140 FROM 1,2-AZIDOALCOHOLS [2, 31
141 CONCLUSIONS 141 REFERENCES 142 METALATED EPOXIDES AND AZIRIDINES IN
SYNTHESIS 145 DAVID M. HODGSON AND CHSSSIOPHER D. BRAY INTRODUCTION 145
METALATED EPOXIDES 146 C-H INSERTIONS 147 TRANSANNULAR C-H INSERTIONS IN
EPOXIDES OF MEDIUM-SIZED CYCLOALKENES 147 TRANSANNULAR C-H INSERTIONS IN
EPOXIDES OF POLYCYCLIC ALKENES 151 NONTRANSANNULAR EXAMPLES OF C-H
INSERTION 152 ISOMERIZATION OF EPOXIDES TO KETONES 153 CYCLOPROPANATIONS
155 OLEFIN FORMATION 157 XI1 TABLE OF CONTENTS I ELEAROPHILE TRAPPING
163 INTRODUCTION 163 SILYL-STABILIZED LITHIATED EPOXIDES 164
SULFONYL-STABILIZED LITHIATED EPOXIDES 165 ORGANYL-STABILIZED LITHIATED
EPOXIDES 167 REMOTELY STABILIZED LITHIATED EPOXIDES 170 SIMPLE METALATED
EPOXIDES 171 METALATED AZIRIDINES 172 ELECTROPHILE TRAPPING 173
STABILIZED METALATED AZIRIDINES 173 NONSTABILIZED METALATED AZIRIDINES
175 OLEFIN FORMATION 177 C-H INSERTIONS 178 OUTLOOK 180 REFERENCES 180
METAL-CATALYZED SYNTHESIS OF EPOXIDES 185 HANS ADOLJSSON AND DANIEIU
BALAN INTRODUCTION 185 OXIDANTS AVAILABLE FOR SELECTIVE TRANSITION
METAL-CATALYZED EPOXIDATION 186 EPOXIDATIONS OF OLEFINS CATALYZED BY
EARLY TRANSITION METALS 188 TITANIUM-CATALYZED EPOXIDATIONS 188
VANADIUM-CATALYZED EPOXIDATIONS 192 CHROMIUM-, MOLYBDENUM-, AND
TUNGSTEN-CATALYZED EPOXIDATIONS 195 HOMOGENEOUS SYSTEMS USING MOLYBDENUM
AND TUNGSTEN CATALYSTS AND ALKYL HYDROPEROXIDES OR HYDROGEN PEROXIDE AS
THE TERMINAL OXIDANT 196 HETEROGENEOUS CATALYSTS 199 MANGANESE-CATALYZED
EPOXIDATIONS 201 HYDROGEN PEROXIDE AS TERMINAL OXIDANT 201
MANGANESE-CATALYZED ASYMMETRIC EPOXIDATIONS 204 RHENIUM-CATALYZED
EPOXIDATIONS 208 MT0 AS EPOXIDATION CATALYST - ORIGINAL FINDINGS 21 1
THE INFLUENCE OF HETEROCYCLIC ADDITIVES 21 1 THE ROLE OF THE ADDITIVE
214 OTHER OXIDANTS 215 SOLVENTS/MEDIA 217 ASYRNMETRIC EPOXIDATIONS WITH
MT0 218 IRON-CATALYZED EPOXIDATIONS 21 9 RUTHENIUM-CATALYZED
EPOXIDATIONS 221 CONCLUDING REMARKS 224 REFERENCES 225 TABLE OF CONTENTS
L X 11 CATALYTIC ASYMMETRIE EPOXIDE RING-OPENING CHEMISTRY 229 LARS P.
C. NIELSEN AND ERIC N. JACOBSEN INTRODUCTION 229 ENANTIOSELECTIVE
NUCLEOPHILIC ADDITION TO MESO-EPOXIDES 229 NITROGEN-CENTERED
NUCLEOPHILES 229 SULFUR-CENTERED NUCLEOPHILES 236 OXYGEN-CENTERED
NUCLEOPHILES 238 CARBON-CENTERED NUCLEOPHILES 243 HALIDE AND HYDRIDE
NUCLEOPHILES 247 KINETIC RESOLUTION OF RACEMIC EPOXIDES 250
NITROGEN-CENTERED NUCLEOPHILES 250 OXYGEN-CENTERED NUCLEOPHILES 255
CARBON-CENTERED NUDEOPHILES 261 ENANTIOSELECTIVE REARRANGEMENTS OF
EPOXIDES 263 CONCLUSION 266 REFERENCES 266 EPOXIDES IN COMPLEX MOLECULE
SYNTHESIS 271 PAOLO CROTTI AND MAURO PINESCHI LNTRODUCTION 271 SYNTHESIS
OF COMPLEX MOLECULES BY INTRAMOLECULAR RING-OPENING OF EPOXIDES WITH
HETERONUDEOPHILES 27 2 INTRAMOLECULAR C-0 BOND-FORMING REACTIONS 271
SYNTHESIS OF SUBSTITUTED THF RINGS 272 SYNTHESIS OF SUBSTITUTED THP
RINGS 275 LNTRAMOLECULAR 5-EXO AND 6-END0 CYCLIZATION OF POLYEPOXIDES
282 INTRAMOLECULAR C-N BOND-FORMING REACTIONS 286 SYNTHESIS OF COMPLEX
MOLECULES BY RING-OPENING OF EPOXIDES WITH C-NUCLEOPHILES 288
INTRAMOLECULAR C-C BOND-FORMING REACTIONS 288 INTERMOLECULAR C-C
BOND-FORMING REACTIONS 290 INTERMOLECULAR C-C BOND-FORMING REACTIONS
WITH ORGANOMETALLIC REAGENTS 290 ADDITION REACTIONS OF META1 ENOLATES OF
NON-STABILIZED ESTERS, AMIDES, AND KETONES TO EPOXIDES 295 EPOXY GLYCALS
299 SYNTHESIS OF COMPLEX MOLECULES BY REARRANGEMENT REACTIONS OF
EPOXIDES 302 REFERENCES 309 VINYLEPOXIDES IN ORGANIC SYNTHESIS 315 BERIT
OLOFSSON AND PETER SOMFAI SYNTHESIS OF VINYLEPOXIDES 315 VINYLEPOXIDES
FROM UNFUNCTIONALIZED DIENES 316 EPOXIDATION WITH DIOXIRANES 31 6 XIV
TABLE OF CONTENTS I EPOXIDATION WITH MN-SALEN CATALYSTS 318 CONVERSION
OF DIOLS INTO EPOXIDES 31 9 VINYLEPOXIDES FROM FUNCTIONALIZED DIENES 320
FROM DIENONES OR UNSATURATED AMIDES 320 FROM DIENOLS 321 VINYLEPOXIDES
FROM EPOXY ALCOHOLS 322 VINYLEPOXIDES FROM ALDEHYDES 324
CHLOROALLYLBORATION 324 REACTION WITH SULFUR YLIDES 326 VINYLEPOXIDES
FROM OTHER SUBSTRATES 327 FROM ALLENES 327 KINETIC RESOLUTION OF RACEMIC
EPOXIDES 328 TRANSFORMATIONS OF VINYLEPOXIDES 329 [NTERMOLECULAR OPENING
WITH OXYGEN AND NITROGEN NUCLEOPHILES 329 1.2-ADDITIONS 329
1,4-ADDITIONS 331 INTRAMOLECULAR OPENING WITH OXYGEN AND NITROGEN
NUCLEOPHILES 332 OPENING WITH CARBON NUCLEOPHILES 335 SN2 ADDITIONS 335
SN^ ADDITIONS 337 REGIODIVERGENT ADDITIONS 338 REARRANGEMENT REACTIONS
338 HYDROGENOLYSIS 341 CONCLUSIONS 343 REFERENCES 343 THE BIOSYNTHESIS
OF EPOXIDES 349 SABINE GRIISCHOW AND DAVID H. SHERMAN INTRODUCTION 349
CYTOCHROME P450 MONOOXYGENASES 350 MECHANISM OF CYTOCHROME P450
MONOOXYGENASES 350 EPOTHILONES 355 MYCINAMICIN 362 GRISEORHODIN A 364
HEDAMYCIN 367 FLAVIN-DEPENDENT EPOXIDASES 368 SQUALENE EPOXIDASE 368
STYRENE EPOXIDASE 373 DIOXYGENASES 376 EPOXIDATION THROUGH
DEHYDROGENATION 383 FOSFOMYCIN 383 SCOPOLARNINE 387 DEHALOGENASES 389
SUMMARY AND OUTLOOK 394 REFERENCES 394 TABLE OF CONTENTS I AZIRIDINE
NATURAL PRODUCTS - DISCOVERY, BIOLOGICAL ACTIVITY AND BIOSYNTHESIS 399
PHILIP A. S. LOWDEN INTRODUCTION AND OVEMEW 399 MITOMYCINS AND RELATED
NATURAL PRODUCTS 400 DISCOVERY AND ANTICANCER PROPERTIES 400 MODE OF
ACTION 401 BIOSYNTHESIS 406 THE AZINOMYCINS 414 DISCOVERY AND ANTICANCER
PROPERTIES 4 14 MODE OF ACTION 415 BIOSYNTHESIS 423 OTHER AZIRIDINE
NATURAL PRODUCTS 428 FICELLOMYCIN 428 593ALNSC-135758 428
DICARBOXYAZIRIDINE AND MIRAZIRIDINE A 429 AZICERNICINS 430 MADUROPEPTIN
430 THE MADURASTATINS 433 AZIRIDINE METABOLITES FROM AMINO ALCOHOLS 434
AZIRINE AND DIAZIRINE NATURAL PRODUCTS 435 REFERENCES 437 EPOXIDES AND
AZIRIDINES IN CLICK CHEMISTRY 443 VALERY V FOKIN AND PENG WU
INTRODUCTION 443 EPOXIDES IN CLICK CHEMISTRY 447 SYNTHESIS OF EPOXIDES
447 NUCLEOPHILIC OPENING OF EPOXIDES 451 AZIRIDINES IN CLICK CHEMISTRY
455 SYNTHESIS OF AZIRIDINES 455 BROMINE-CATALYZED AZIRIDINATION OF
OLEFINS WITH CHLORAMINES 455 AMINOHYDROXYLATION FOLLOWED BY
CYCLODEHYDRATION 459 NUCLEOPHILIC OPENING OF AZIRIDINES 467 AZIRIDINIUM
IONS IN CLICK CHEMISTRY 470 GENERATION OF AZIRIDINIUM IONS 470
NUDEOPHILIC OPENING OF AZIRIDINIUM IONS 471 SYNTHESIS OF DIAMINO ESTERS
AND P-LACTAMS 472 SYNTHESIS OF PYRAZOLO[L,2-A]PYRAZOLES 473 REFERENCES
475 INDEX 479
|
| adam_txt |
TABLE OF CONTENTS FOREWORD V11 PREFACE XVII LIST OF CONTRIBUTORS XIX
ASYMMETRIC SYNTHESIS OF EPOXIDES AND AZIRIDINES FIOM ALDEHYDES AND
IMINES 1 VARINDER K. AGGANVAL, D. MICHAEL BADINE, UND VIJAYALAKSHMI A.
MOORTHIE INTRODUCTION 1 ASYMMETRIC EPOXIDATION OF CARBONYL COMPOUNDS 1
ARYL, VINYL, AND ALKYL EPOXIDES 2 STOICHIOMETRIC YLIDE-MEDIATED
EPOXIDATION 2 CATALYTIC YLIDE-MEDIATED EPOXIDATION 3 DISCUSSION OF
FACTORS AFFECTING DIASTEREO- AND ENANTIOSELECTIVITY 8 TERMINAL EPOXIDES
10 EPOXY ESTERS, AMIDES, ACIDS, KETONES, AND SULFONES 11 SULFUR
YLIDE-MEDIATED EPOXIDATION 1 1 DARZENS REACTION 13 DARZENS REACTIONS IN
THE PRESENCE OF CHIRAL AUXILIARIES 13 DARZENS REACTIONS WITH CHIRAL
REAGENTS 18 DARZENS REACTIONS WITH CHIRAL CATALYSTS 20 ASYMMETRIC
AZIRIDINATION OF IMINES 22 AZIRIDINES BEARING ELEDRON-WITHDRAWING
GROUPS: ESTERS AND AMIDES 23 AZA-DARZENS ROUTE 23 REACTIONS BETWEEN
IMINES AND CARBENES 24 AZIRIDINES BY GUANIDINIUM YLIDE CHEMISTRY 27
AZIRIDINES BEARING ALKYL, ARYL, PROPARGYL, AND VINYL GROUPS 28 ARYL,
VINYL, AND ALKYL AZIRIDINES: STOICHIOMETRIC ASYMMETRIC YLIDE-MEDIATED
AZIRIDINATION 28 ARYL, VINYL, AND ALKYL AZIRIDINES: CATALYTIC ASYMMETRIC
YLIDE-MEDIATED AZIRIDINATION 31 SUMMARY AND OUTLOOK 33 REFERENCES 34
AZIRIDINES OND EPOXIDES IN ORGANIC SYNTHESIS. ANDREI K. YUDIN COPYRIGHT
0 2006 WILEY-VCH VERLAG GMBH & CO. KGAA, WEINHEIM ISBN: 3-527-31213-7 X
TABLE OFCONTENTS I VINYLAZIRIDINES IN ORGANIC SYNTHESIS 37 HIROAKI OHNO
LNTRODUCTION 37 DIRECI SYNTHESIS OF VINYLAZIRIDINES [I] 37 ADDITION OF
NITRENE TO DIENES 37 ADDITION OF ALLYLIC YLIDES AND RELATED REAGENTS TO
IMINES 39 CYDIZATION OF AMINO ALCOHOLS AND RELATED COMPOUNDS 42
CYDIZATION OF AMINO ALLENES 45 AZIRIDINATION OF A,SS-UNSATURATED OXIMES
AND HYDRAZONES 46 RING-OPENING REACTIONS WITH NUCLEOPHILES 47 HYDRIDE
REDUCTION 47 ORGANOCOPPER-MEDIATED ALKYLATION 48 REACIIONS WITH OXYGEN
NUCLEOPHILES 51 REACTIONS WITH OTHER NUCLEOPHILES 54 LSOMERIZATION
INCLUDING REARRANGEMENT 54 AZA-[3,3]-CLAISEN REARRANGEMENT 55 PYRROLINE
FORMATION 57 AZA-[L, 31-WITTIG REARRANGEMENT 60 HYDROGEN SHIFI 61
REARRANGEMENT WITH AN ARYL GROUP ON THE AZIRIDINE CARBON 62
EPIMERIZATION 63 CYDOADDITION 64 CYDOADDITIONS OF LSOCYANATES AND
RELATED COMPOUNDS 64 CARBONYLATIVE RING-EXPANSION TO LACTAMS 65 ELECTRON
TRANSFER TO VINYLAZIRIDINES 67 CONDUSIONS 68 REFERENCES 68 ASYMMETRIE
SYNTHESES WITH AZIRIDINECARBOXYLATE AND AZIRIDINE- PHOSPHONATE BUILDING
BLOCKS 73 PING ZHOU, BANG-CHI CHEN, AND FRANKLIN A. DAVIS LNTRODUCTION
73 PREPARATION OF AZIRIDINE-2-CARBOXYLATES AND AZIRIDINE-2-PHOSPHO-
NATES 74 PREPARATION OF AZIRIDINE -2-CARBOXYLATES 74 CYCLIZATION OF
HYDROXY AMINO ESTERS 74 CYCLIZATION OF HYDROXY AZIDO ESTERS 76
CYDIZATION OF A-HALO- AND A-SULFONYLOXY-SS-ARNINO ESTERS AND AMIDES 76
AZIRIDINATION OF A,SS-UNSATURATED ESTERS 77 AZIRIDINATION OF IMINES 79
AZIRIDINATION OF ALDEHYDES 82 2-CARBOXYLATION OF AZIRIDINES 83
RESOLUTION OF RACEMIC AZIRIDINE-2-CARBOXYLATES 84 PREPARATION OF
AZIRIDINE-2-PHOSPHONATES 85 TABLE OF CONTENTS I X' REACTIONS OF
AZINDINE-2-CARBOXYLATES AND AZIRIDINE-2-PHOSPHO- NATES 87 REACTIONS OF
AZIRIDINE-2-CARBOXYLATES 87 REDUCTIVE RING-OPENING 88 BASE-PROMOTED
RING-OPENING 89 NUCLEOPHILIC RING-OPENING 89 ELECTROPHILIC SUBSTITUTIONS
AT THE C-2 CARBON ATOM 97 RING-EXPANSION REACTIONS 98 CONVERSION TO
AZIRINE-2-CARBOXYLATES 102 REACTIONS OF AZIRIDINE-2-PHOSPHONATES 103
APPLICATIONS IN NATURAL PRODUCT SYNTHESES 105 SUMMARY AND CONCLUSIONS 11
1 REFERENCES 11 2 SYNTHESIS OF AZIRIDINES 117 DEDICATED, WITH RESPECT,
TO PROFSSOR SIR CHARLES REES, FRS JOSEPH B. SWEENEY INTRODUCTION 117
OVEMIEW AND GENERAL FEATURES 11 7 ADDITION TO ALKENES 118 ADDITION OF
NITRENES AND NITRENOIDS TO ALKENES 119 AZIRIDINES BY
ADDITION-ELIMINATION PROCESSES 128 ADDITION TO IMINES 129 CARBENE
METHODOLOGY 129 AZA-DARZENS AND ANALOGOUS REACTIONS I32 ADDITION TO
AZIRINES 134 AZINDINES THROUGH CYCLIZATION 139 FROM EPOXIDES 139 FROM
1.2-AMINOALCOHOLS AND 1,2-AMINOHALIDES 140 FROM 1,2-AZIDOALCOHOLS [2, 31
141 CONCLUSIONS 141 REFERENCES 142 METALATED EPOXIDES AND AZIRIDINES IN
SYNTHESIS 145 DAVID M. HODGSON AND CHSSSIOPHER D. BRAY INTRODUCTION 145
METALATED EPOXIDES 146 C-H INSERTIONS 147 TRANSANNULAR C-H INSERTIONS IN
EPOXIDES OF MEDIUM-SIZED CYCLOALKENES 147 TRANSANNULAR C-H INSERTIONS IN
EPOXIDES OF POLYCYCLIC ALKENES 151 NONTRANSANNULAR EXAMPLES OF C-H
INSERTION 152 ISOMERIZATION OF EPOXIDES TO KETONES 153 CYCLOPROPANATIONS
155 OLEFIN FORMATION 157 XI1 TABLE OF CONTENTS I ELEAROPHILE TRAPPING
163 INTRODUCTION 163 SILYL-STABILIZED LITHIATED EPOXIDES 164
SULFONYL-STABILIZED LITHIATED EPOXIDES 165 ORGANYL-STABILIZED LITHIATED
EPOXIDES 167 REMOTELY STABILIZED LITHIATED EPOXIDES 170 SIMPLE METALATED
EPOXIDES 171 METALATED AZIRIDINES 172 ELECTROPHILE TRAPPING 173
STABILIZED METALATED AZIRIDINES 173 NONSTABILIZED METALATED AZIRIDINES
175 OLEFIN FORMATION 177 C-H INSERTIONS 178 OUTLOOK 180 REFERENCES 180
METAL-CATALYZED SYNTHESIS OF EPOXIDES 185 HANS ADOLJSSON AND DANIEIU
BALAN INTRODUCTION 185 OXIDANTS AVAILABLE FOR SELECTIVE TRANSITION
METAL-CATALYZED EPOXIDATION 186 EPOXIDATIONS OF OLEFINS CATALYZED BY
EARLY TRANSITION METALS 188 TITANIUM-CATALYZED EPOXIDATIONS 188
VANADIUM-CATALYZED EPOXIDATIONS 192 CHROMIUM-, MOLYBDENUM-, AND
TUNGSTEN-CATALYZED EPOXIDATIONS 195 HOMOGENEOUS SYSTEMS USING MOLYBDENUM
AND TUNGSTEN CATALYSTS AND ALKYL HYDROPEROXIDES OR HYDROGEN PEROXIDE AS
THE TERMINAL OXIDANT 196 HETEROGENEOUS CATALYSTS 199 MANGANESE-CATALYZED
EPOXIDATIONS 201 HYDROGEN PEROXIDE AS TERMINAL OXIDANT 201
MANGANESE-CATALYZED ASYMMETRIC EPOXIDATIONS 204 RHENIUM-CATALYZED
EPOXIDATIONS 208 MT0 AS EPOXIDATION CATALYST - ORIGINAL FINDINGS 21 1
THE INFLUENCE OF HETEROCYCLIC ADDITIVES 21 1 THE ROLE OF THE ADDITIVE
214 OTHER OXIDANTS 215 SOLVENTS/MEDIA 217 ASYRNMETRIC EPOXIDATIONS WITH
MT0 218 IRON-CATALYZED EPOXIDATIONS 21 9 RUTHENIUM-CATALYZED
EPOXIDATIONS 221 CONCLUDING REMARKS 224 REFERENCES 225 TABLE OF CONTENTS
L X'11 CATALYTIC ASYMMETRIE EPOXIDE RING-OPENING CHEMISTRY 229 LARS P.
C. NIELSEN AND ERIC N. JACOBSEN INTRODUCTION 229 ENANTIOSELECTIVE
NUCLEOPHILIC ADDITION TO MESO-EPOXIDES 229 NITROGEN-CENTERED
NUCLEOPHILES 229 SULFUR-CENTERED NUCLEOPHILES 236 OXYGEN-CENTERED
NUCLEOPHILES 238 CARBON-CENTERED NUCLEOPHILES 243 HALIDE AND HYDRIDE
NUCLEOPHILES 247 KINETIC RESOLUTION OF RACEMIC EPOXIDES 250
NITROGEN-CENTERED NUCLEOPHILES 250 OXYGEN-CENTERED NUCLEOPHILES 255
CARBON-CENTERED NUDEOPHILES 261 ENANTIOSELECTIVE REARRANGEMENTS OF
EPOXIDES 263 CONCLUSION 266 REFERENCES 266 EPOXIDES IN COMPLEX MOLECULE
SYNTHESIS 271 PAOLO CROTTI AND MAURO PINESCHI LNTRODUCTION 271 SYNTHESIS
OF COMPLEX MOLECULES BY INTRAMOLECULAR RING-OPENING OF EPOXIDES WITH
HETERONUDEOPHILES 27 2 INTRAMOLECULAR C-0 BOND-FORMING REACTIONS 271
SYNTHESIS OF SUBSTITUTED THF RINGS 272 SYNTHESIS OF SUBSTITUTED THP
RINGS 275 LNTRAMOLECULAR 5-EXO AND 6-END0 CYCLIZATION OF POLYEPOXIDES
282 INTRAMOLECULAR C-N BOND-FORMING REACTIONS 286 SYNTHESIS OF COMPLEX
MOLECULES BY RING-OPENING OF EPOXIDES WITH C-NUCLEOPHILES 288
INTRAMOLECULAR C-C BOND-FORMING REACTIONS 288 INTERMOLECULAR C-C
BOND-FORMING REACTIONS 290 INTERMOLECULAR C-C BOND-FORMING REACTIONS
WITH ORGANOMETALLIC REAGENTS 290 ADDITION REACTIONS OF META1 ENOLATES OF
NON-STABILIZED ESTERS, AMIDES, AND KETONES TO EPOXIDES 295 EPOXY GLYCALS
299 SYNTHESIS OF COMPLEX MOLECULES BY REARRANGEMENT REACTIONS OF
EPOXIDES 302 REFERENCES 309 VINYLEPOXIDES IN ORGANIC SYNTHESIS 315 BERIT
OLOFSSON AND PETER SOMFAI SYNTHESIS OF VINYLEPOXIDES 315 VINYLEPOXIDES
FROM UNFUNCTIONALIZED DIENES 316 EPOXIDATION WITH DIOXIRANES 31 6 XIV
TABLE OF CONTENTS I EPOXIDATION WITH MN-SALEN CATALYSTS 318 CONVERSION
OF DIOLS INTO EPOXIDES 31 9 VINYLEPOXIDES FROM FUNCTIONALIZED DIENES 320
FROM DIENONES OR UNSATURATED AMIDES 320 FROM DIENOLS 321 VINYLEPOXIDES
FROM EPOXY ALCOHOLS 322 VINYLEPOXIDES FROM ALDEHYDES 324
CHLOROALLYLBORATION 324 REACTION WITH SULFUR YLIDES 326 VINYLEPOXIDES
FROM OTHER SUBSTRATES 327 FROM ALLENES 327 KINETIC RESOLUTION OF RACEMIC
EPOXIDES 328 TRANSFORMATIONS OF VINYLEPOXIDES 329 [NTERMOLECULAR OPENING
WITH OXYGEN AND NITROGEN NUCLEOPHILES 329 1.2-ADDITIONS 329
1,4-ADDITIONS 331 INTRAMOLECULAR OPENING WITH OXYGEN AND NITROGEN
NUCLEOPHILES 332 OPENING WITH CARBON NUCLEOPHILES 335 SN2' ADDITIONS 335
SN^ ADDITIONS 337 REGIODIVERGENT ADDITIONS 338 REARRANGEMENT REACTIONS
338 HYDROGENOLYSIS 341 CONCLUSIONS 343 REFERENCES 343 THE BIOSYNTHESIS
OF EPOXIDES 349 SABINE GRIISCHOW AND DAVID H. SHERMAN INTRODUCTION 349
CYTOCHROME P450 MONOOXYGENASES 350 MECHANISM OF CYTOCHROME P450
MONOOXYGENASES 350 EPOTHILONES 355 MYCINAMICIN 362 GRISEORHODIN A 364
HEDAMYCIN 367 FLAVIN-DEPENDENT EPOXIDASES 368 SQUALENE EPOXIDASE 368
STYRENE EPOXIDASE 373 DIOXYGENASES 376 EPOXIDATION THROUGH
DEHYDROGENATION 383 FOSFOMYCIN 383 SCOPOLARNINE 387 DEHALOGENASES 389
SUMMARY AND OUTLOOK 394 REFERENCES 394 TABLE OF CONTENTS I AZIRIDINE
NATURAL PRODUCTS - DISCOVERY, BIOLOGICAL ACTIVITY AND BIOSYNTHESIS 399
PHILIP A. S. LOWDEN INTRODUCTION AND OVEMEW 399 MITOMYCINS AND RELATED
NATURAL PRODUCTS 400 DISCOVERY AND ANTICANCER PROPERTIES 400 MODE OF
ACTION 401 BIOSYNTHESIS 406 THE AZINOMYCINS 414 DISCOVERY AND ANTICANCER
PROPERTIES 4 14 MODE OF ACTION 415 BIOSYNTHESIS 423 OTHER AZIRIDINE
NATURAL PRODUCTS 428 FICELLOMYCIN 428 593ALNSC-135758 428
DICARBOXYAZIRIDINE AND MIRAZIRIDINE A 429 AZICERNICINS 430 MADUROPEPTIN
430 THE MADURASTATINS 433 AZIRIDINE METABOLITES FROM AMINO ALCOHOLS 434
AZIRINE AND DIAZIRINE NATURAL PRODUCTS 435 REFERENCES 437 EPOXIDES AND
AZIRIDINES IN CLICK CHEMISTRY 443 VALERY V FOKIN AND PENG WU
INTRODUCTION 443 EPOXIDES IN CLICK CHEMISTRY 447 SYNTHESIS OF EPOXIDES
447 NUCLEOPHILIC OPENING OF EPOXIDES 451 AZIRIDINES IN CLICK CHEMISTRY
455 SYNTHESIS OF AZIRIDINES 455 BROMINE-CATALYZED AZIRIDINATION OF
OLEFINS WITH CHLORAMINES 455 AMINOHYDROXYLATION FOLLOWED BY
CYCLODEHYDRATION 459 NUCLEOPHILIC OPENING OF AZIRIDINES 467 AZIRIDINIUM
IONS IN CLICK CHEMISTRY 470 GENERATION OF AZIRIDINIUM IONS 470
NUDEOPHILIC OPENING OF AZIRIDINIUM IONS 471 SYNTHESIS OF DIAMINO ESTERS
AND P-LACTAMS 472 SYNTHESIS OF PYRAZOLO[L,2-A]PYRAZOLES 473 REFERENCES
475 INDEX 479 |
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| id | DE-604.BV021528577 |
| illustrated | Illustrated |
| index_date | 2024-07-02T14:24:38Z |
| indexdate | 2024-07-09T20:37:53Z |
| institution | BVB |
| isbn | 3527312137 9783527312139 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-014744957 |
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| physical | XXI, 492 S. graph. Darst. 240 mm x 170 mm |
| publishDate | 2006 |
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| publisher | WILEY-VCH |
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| spelling | Aziridines and epoxides in organic synthesis ed. by Andrei K. Yudin Weinheim WILEY-VCH 2006 XXI, 492 S. graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Composés organiques - Synthèse Époxydes Aziridines Epoxy compounds Organic compounds Synthesis Aziridine (DE-588)4143796-2 gnd rswk-swf Epoxide (DE-588)4152561-9 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Epoxide (DE-588)4152561-9 s Organische Synthese (DE-588)4075695-6 s DE-604 Aziridine (DE-588)4143796-2 s Judin, Andrej K. Sonstige oth OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014744957&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Aziridines and epoxides in organic synthesis Composés organiques - Synthèse Époxydes Aziridines Epoxy compounds Organic compounds Synthesis Aziridine (DE-588)4143796-2 gnd Epoxide (DE-588)4152561-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4143796-2 (DE-588)4152561-9 (DE-588)4075695-6 |
| title | Aziridines and epoxides in organic synthesis |
| title_auth | Aziridines and epoxides in organic synthesis |
| title_exact_search | Aziridines and epoxides in organic synthesis |
| title_exact_search_txtP | Aziridines and epoxides in organic synthesis |
| title_full | Aziridines and epoxides in organic synthesis ed. by Andrei K. Yudin |
| title_fullStr | Aziridines and epoxides in organic synthesis ed. by Andrei K. Yudin |
| title_full_unstemmed | Aziridines and epoxides in organic synthesis ed. by Andrei K. Yudin |
| title_short | Aziridines and epoxides in organic synthesis |
| title_sort | aziridines and epoxides in organic synthesis |
| topic | Composés organiques - Synthèse Époxydes Aziridines Epoxy compounds Organic compounds Synthesis Aziridine (DE-588)4143796-2 gnd Epoxide (DE-588)4152561-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Composés organiques - Synthèse Époxydes Aziridines Epoxy compounds Organic compounds Synthesis Aziridine Epoxide Organische Synthese |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014744957&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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