Catalytic asymmetric conjugate reactions:
Gespeichert in:
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2010
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| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Beschreibung: | XVII, 447 S. Ill., graph. Darst. |
| ISBN: | 9783527324118 |
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CONTENTS PREFACE XIII LIST OF CONTRIBUTORS XV 1 RHODIUM-AND
PALLADIUM-CATALYZED ASYMMETRIC CONJUGATE ADDITIONS 1 GUILLAUME BERTHON
AND TAMIO HAYASHI 1.1 INTRODUCTION 1 1.2 RH-CATALYZED ECA OF ORGANOBORON
REAGENTS 1 1.2.1 A,SS-UNSATURATED RETONES 2 1.2.1.1 A SHORT HISTORY 2
1.2.1.2 CATALYTIC CYCLE 4 1.2.1.3 MODEL FOR ENANTIOSELECTION 7 1.2.1.4
ORGANOBORON SOURCES OTHER THAN BORONIC ACIDS 9 1.2.1.5 RH PRECATALYSTS
10 1.2.1.6 LIGAND SYSTEMS 11 1.2.1.7 BIDENTATE PHOSPHORUS LIGAND 11
1.2.1.8 MONODENTATE LIGAND 14 1.2.1.9 DIENE LIGANDS 16 1.2.1.10
BIS-SULFOXIDE 18 1.2.1.11 MIXED DONOR LIGANDS 19 1.2.1.12 TRAPPING OF
BORON ENOLATES 19 1.2.1.13 A,SS-UNSATURATED ALDEHYDES 20 1.2.2
CT,SS-UNSATURATED ESTERS AND AMIDES 22 1.2.2.1 DIASTEREOSELECTIVE
CONJUGATE ADDITION 26 1.2.2.2 FUMARATE AND MALEIMIDES 26 1.2.2.3
SYNTHETICALLY USEFUL ACCEPTORS FOR RH-CATALYZED ECAS 29 BIBLIOGRAFISCHE
INFORMATIONEN HTTP://D-NB.INFO/1000249964 DIGITALISIERT DURCH VI
CONTENTS 1.6 RH-CATALYZED ECA OF AJKYNES 44 1.7 RH-CATALYZED TANDEM
PROCESSES 47 1.7.1 TANDEM ECA/ALDOL REACTION 47 1.7.2 TANDEM CONJUGATE
ADDITION/1,2-ADDITION 48 1.7.3 TANDEM ECA/MANNICH REACTION 49 1.7'.4
TANDEM CONJUGATE ADDITION/MICHAEL CYCLIZATION 50 1.7.5 TANDEM
CARBORHODATION/CONJUGATE ADDITION 50 1.8 1,6-CONJUGATE ADDITIONS 54 1.9
PD-CATALYZED ECA 56 1.9.1 CATALYTIC CYCLE 62 1.10 CONCLUSIONS 63
REFERENCES 64 2 CU- AND NI-CATALYZED CONJUGATED ADDITIONS OF ORGANOZINCS
AND ORGANOALUMINUMS TO A,SS-UNSATURATED CARBONYL COMPOUNDS 71 MARTIN
KOTORA AND ROBERT BETIK 2.1 INTRODUCTION 71 2.2 GENERAL ASPECTS 72 2.2.1
PROPERTIES OF ORGANOZINC AND ORGANOALUMINUM COMPOUNDS 72 2.2.1.1
REACTION MECHANISMS OF CU-CATALYZED CONJUGATED ADDITION 72 2.2.1.2
REACTION MECHANISMS OF NI-CATALYZED CONJUGATED ADDITION 73 2.2.2
PREPARATION OF ORGANOZINC COMPOUNDS 74 2.2.2.1 PREPARATION BY A DIRECT
INSERTION INTO THE CARBON-HALIDE BOND 74 2.2.2. CONTENTS VII
CU-CATALYZED ASYMMETRIC CONJUGATED ADDITION OF ME 3 AL TO
5-METHYLPENT-3-EN-2-ONE IN THE PRESENCE OF L2D [74] 118 CU-CATALYZED
CONJUGATED ADDITION OF ET2ZN TO
(E)-L-[(3-PHENYL)ACRYLOYL]PYRROLIDIN-2-ONE IN THE PRESENCE OFL2D[62] 118
CU-CATALYZED CONJUGATED ADDITION OF ()-(2-PHENYL-L-PROPEN-L-YL)
DIMETHYLALUMINUM TO CYCLOHEXENONE IN THE PRESENCE OF L2D [74] 119
CU-CATALYZED ASYMMETRIC CONJUGATED ADDITION OF ET2ZN TO CYCLOHEPTENONE
IN THE PRESENCE OF L8 [70] 119 CU-CATALYZED CONJUGATED ADDITION OF
I-P^ZN TO 1-ACETYLCYCLOPENTENE IN THE PRESENCE OF LI 2 [80] 120
CU-CATALYZED CONJUGATED ADDITION OF ET2ZN TO
[3-[6-(TERT-BUTYLDIMETHYLSILANYLOXY)HEX-2-ENOYL]OXAZOLIDIN-2-ONE IN THE
PRESENCE OF L14 [83] 120 CU-CATALYZED CONJUGATED ADDITION OF ET2ZN TO
4,4-(DIMETHYL)CYCLOHEXENONE IN THE PRESENCE OF L25 [92] 121 CU-CATALYZED
CONJUGATED ADDITION OF DIETHYLZINC TO 3,3-DIMETHOXY-L-NITRO-L-PROPENE IN
THE PRESENCE OF L5A [67] 121 CU-CATALYZED CONJUGATED ADDITION OF PH 2 ZN
TO 3-MEMYKYCLORIEXENONE IN THE PRESENCE L38B [116] 122 CU-CATALYZED
CONJUGATED ADDITION OF [ACO(CH2)4J2ZN TO TERT-BUTY VILI I CONTENTS
2.6.2.6 SYNTHESIS OF (*)-PUMILIOTOXIN C 134 2.6.2.7 SYNTHESIS OF
PHTHIOCEROL 135 2.6.2.8 SYNTHESIS OF LEAF MINER PHEROMONES 135 2.6.2.9
SYNTHESIS OF SS-AMINO ACIDS 136 2.6.2.10 SYNTHESIS OF CLAVULARIN B 336
2.6.2.11 FORMAL SYNTHESIS OF AXANES 137 2.7 CONCLUSIONS 137 REFERENCES
138 3 ECAS OF ORGANOLITHIUM REAGENTS, GRIGNARD REAGENTS, AND EXAMPLES OF
CU-CATALYZED ECAS 245 GUI-LING ZHAO AND ARMANDO CORDOVA 3.1 INTRODUCTION
145 3.2 ENANTIOSELECTIVE CONJUGATE ADDITION OF LITHIUM REAGENTS 145 3.3
CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD REAGENTS 152
3.4 CU-COMPLEXES AS CATALYSTS FOR ENANTIOSELECTIVE CONJUGATE ADDITIONS
159 3.5 CONCLUSIONS 164 REFERENCES 164 4 ASYMMETRIC BIFUNCTIONAL
CATALYSIS USING HETEROBIMETALLIC AND MULTIMETALLIC SYSTEMS IN
ENANTIOSELECTIVE CONJUGATE ADDITIONS 169 ARMANDO CORDOVA 4.1
INTRODUCTION 169 4.2 DINUCLEAR ZN-COMPLEXES IN CATALYTIC ECAS 171 4.
CONTENTS IX 5.3.4 OTHER REACTIONS 204 5.4 ALDEHYDE CONJUGATE ADDITIONS
205 5.4.1 ALDEHYDE CONJUGATE ADDITIONS TO NITROOLEFINS 206 5.4.2
ALDEHYDE CONJUGATE ADDITIONS TO VINYL SULFONES 208 5.4.3 OTHER REACTIONS
209 5.5 TANDEM OR CASCADE REACTIONS 212 5.6 CONCLUSIONS 214 5.7
EXPERIMENTAL 215 KETONE ADDITION TO NITROSTYRENES (AS REPORTED BY LIST
[12]) 215 ASYMMETRIC MICHAEL REACTION OF ALDEHYDES AND NITROALKENES (AS
REPORTED BY HAYASHI [49]) 215 CATALYTIC CONJUGATE ADDITION OF ALDEHYDES
TO VINYL SULFONES (AS REPORTED BY PALOMO [57]) 215 GENERAL PROCEDURE FOR
THE SYNTHESIS OF CYCLOHEXENE DERIVATIVES (AS REPORTED BY ENDERS [67])
215 REFERENCES 226 6 IMINIUM ACTIVATION IN CATALYTIC ENANTIOSELECTIVE
CONJUGATE ADDITIONS 2I9 JOSE L. VICARIO, EFRAIM REYES, DOLORES BADIA,
AND LUISA CARRILLO 6.1 INTRODUCTION 219 6.2 MECHANISTIC ASPECTS OF THE
IMINIUM ACTIVATION CONCEPT, AND FACTORS INFLUENCING STEREOCONTROL IN
MICHAEL ADDITIONS 220 6.3 MICHAEL REACTIONS 224 6.3.1 1,3-DICARBONYL
COMPOUNDS AS NUCLEOPHILES 224 X CONTENTS 6.7.8 CASCADE PROCESSES
INITIATED BY CONJUGATE FRIEDEL-CRAFTS REACTION 277 6.7.9 CASCADE
PROCESSES INITIATED BY CONJUGATE HYDROGEN-TRANSFER REACTION 280 6.7.10
CASCADE PROCESSES INITIATED BY HETERO-MICHAEL REACTIONS 282 6.8
CONCLUDING REMARKS AND OUTLOOK 287 REFERENCES 287 7 ORGANOCATALYTIC
ENANTIOSELECTIVE CONJUGATE ADDITIONS OF H ETERNATO M S TO
OI,SS-UNSATURATED CARBONYL COMPOUNDS 295 SHILEI ZHANG AND WEI WANG 7.1
INTRODUCTION 295 7.2 "AT" AS NUCLEOPHILES 295 7.2.1 INTERMOLECULAR
AZA-MICHAEL REACTIONS 295 7.2.2 INTRAMOLECULAR AZA-MICHAEL REACTIONS 299
7.2.3 NITROGEN INITIATED AZA-MICHAEL CASCADE REACTIONS 300 7.3 "O" AS
NUCLEOPHILES 304 7.3.1 INTERMOLECULAR OXA-MICHAEL REACTIONS 304 7.3.2
INTRAMOLECULAR OXA-MICHAEL REACTIONS 306 7.3.3 OXYGEN-INITIATED
OXA-MICHAEL CASCADE REACTIONS 307 7.4 "S" AS NUCLEOPHILES 310 7.4.1
INTERMOLECULAR THIA-MICHAEL REACTIONS 320 7.4. CONTENTS XI 9.2
METAL-CATALYZED EPOXIDATIONS 352 9.2.1 EPOXIDATION OF CT,SS-UNSATURATED
KETONES MEDIATED BY CHIRALLY MODIFIED ZN- AND MG-ALKYL PEROXIDES 352
9.2.2 EPOXIDATION OF A,SS-UNSATURATED KETONES, AMIDES, AND ESTERS
MEDIATED BY LANTHANIDE-BINOL SYSTEMS 357 9.3 ORGANOCATALYZED
EPOXIDATIONS 362 9.3.1 PHASE-TRANSFER CATALYSTS 362 9.3.2 POLYAMINO
ACIDS 369 9.3.3 OPTICALLY PURE ALKYL HYDROPEROXIDES OR LIGANDS 373 9.3.4
GUANIDINE-BASED CATALYSTS 376 9.3.5 PYRROLIDINE-BASED CATALYSTS 377
9.3.6 IMIDAZOLIDINONE SALT CATALYSTS 381 9.3.7 PRIMARY AMINES 382 9.4
CONCLUSIONS 385 9.5 EXPERIMENTAL 386 TYPICAL PROCEDURE FOR ASYMMETRIC
EPOXIDATION OF A,SS-UNSATURATED ESTERS [39] 386 ASYMMETRIC EPOXIDATION OF
IRANS-CHALCONE CATALYZED BY DIARYL PROLINOL 90/TBHP SYSTEM [83] 387
REFERENCES 387 10 CATALYTIC ASYMMETRIC BAYLIS-HILLMAN REACTIONS AND
SURROUNDINGS 393 GUI-LING ZHAO 10.1 INTRODUCTION 393 10. |
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| spellingShingle | Catalytic asymmetric conjugate reactions Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4135603-2 |
| title | Catalytic asymmetric conjugate reactions |
| title_auth | Catalytic asymmetric conjugate reactions |
| title_exact_search | Catalytic asymmetric conjugate reactions |
| title_full | Catalytic asymmetric conjugate reactions Ed. by Armando Córdova |
| title_fullStr | Catalytic asymmetric conjugate reactions Ed. by Armando Córdova |
| title_full_unstemmed | Catalytic asymmetric conjugate reactions Ed. by Armando Córdova |
| title_short | Catalytic asymmetric conjugate reactions |
| title_sort | catalytic asymmetric conjugate reactions |
| topic | Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd |
| topic_facet | Katalyse Asymmetrische Synthese |
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