Chiral ferrocenes in asymmetric catalysis: synthesis and applications
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2010
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| Item Description: | Literaturangaben |
| Physical Description: | XVII, 414 S. graph. Darst. 25 cm |
| ISBN: | 9783527322800 |
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| 245 | 1 | 0 | |a Chiral ferrocenes in asymmetric catalysis |b synthesis and applications |c ed. by Li-Xin Dai ... |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2010 | |
| 300 | |a XVII, 414 S. |b graph. Darst. |c 25 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Literaturangaben | ||
| 650 | 4 | |a Asymmetric synthesis | |
| 650 | 4 | |a Catalysis | |
| 650 | 4 | |a Chirality | |
| 650 | 4 | |a Ferrocene | |
| 650 | 0 | 7 | |a Katalyse |0 (DE-588)4029921-1 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Chirale Verbindungen |0 (DE-588)4348527-3 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Ferrocenderivate |0 (DE-588)4154117-0 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Ferrocenderivate |0 (DE-588)4154117-0 |D s |
| 689 | 0 | 1 | |a Chirale Verbindungen |0 (DE-588)4348527-3 |D s |
| 689 | 0 | 2 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |D s |
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IMAGE 1
CONTENTS
LIST OF CONTRIBUTORS XV
1 INTRODUCTION 1
UE-XIN DAL AND XUE-LONG HOU 1.1 FOREWORD 1
1.2 PLANAR CHIRALITY OF FERROCENYL LIGANDS 4 1.3 DERIVATIZATION OF THE
FERROCENE SCAFFOLD 6 1.4 STABILITY, RIGIDITY AND BULKINESS OF THE
FERROCENE SCAFFOLD 9 1.5 OUTLOOK 10
REFERENCES 11
2 STEREOSELECTIVE SYNTHESIS OF PLANAR CHIRAL FERROCENES 15 WEI-PING
DENG, VICTOR SNIECKUS, AND COSTA METOILINOS 2.1 INTRODUCTION 15
2.2 DIASTEREOSELECTIVE DIRECTED ORTHO-METALATION OF FERROCENES WITH
CHIRAL AUXILIARIES 19 2.2.1 UGI'S AMINE AND OTHER CHIRAL A-SUBSTIRUTED
FERROCENYLMETHYLAMINES 20 2.2.2 CHIRAL SULFOXIDES 23
2.2.3 CHIRAL ACETALS 26
2.2.4 CHIRAL OXAZOLINES 29
2.2.5 OTHER CHIRAL AUXILIARIES 31 2.3 ENANTIOSELECTIVE DIRECTED
ORTHO-METALATION OF FERROCENES WITH CHIRAL BASES 36 2.4 ENZYMATIC AND
NONENZYMATIC KINETIC RESOLUTIONS 40 2.4.1 ENZYMATIC KINETIC RESOLUTIONS
40 2.4.2 NONENZYMATIC KINETIC RESOLUTIONS 41 2.5 SUMMARY AND
PERSPECTIVES 42
2.6 SELECTED EXPERIMENTAL PROCEDURES 44
CHIRAL FERROCENES IN ASYMMETRIE CATALYSIS. EDITED BY LI-XIN DAI AND
XUE-LONG HOU COPYRIGHT 2010 WILEY-VCH VERLAG GMBH & CO. KGAA, WEINHEIM
ISBN: 978-3-527-32280-0
IMAGE 2
VI CONTENTS
2.6.1 SYNTHESIS OF (R,S P
)-N,N-DIMETHYL-L-(2-DIPHENYLPHOSPHINO-FERROCENYL)
ETHYLAMINE (PPFA) 44 2.6.1.1 SYNTHESIS OF RACEMIC
A-FERROCENYLETHYLDIMETHYLAMINE 44 2.6.1.2 RESOLUTION OF
^FERROCENYLETHYLDIMETHYLARNINE 45 2.6.1.3 SYNTHESIS OF (,S P
)-N,N-DIMETHYL-L-(2-DIPHENYLPHOSPHINOFERK CENYL)
ETHYLAMINE (PPFA} 45 2.6.2 SYNTHESIS OF (,I? P
)-L-(TERT-BUTYLSULFINYL)-2-(DIPHENYLPHOSPHINO)- FERROCENE 45 2.6.2.1
SYNTHESIS OF (-R)-TERT-BUTYLSULFINYLFERROCENE (R) 45 2.6.2.2 SYNTHESIS
OF (R,J? P )-L-(TERT-BUTYLSULFINYL}-2-(DIPHENYLPHOSPHINO)
FERROCENE 46
2.6.3 SYNTHESIS OF FCPHOX 46
2.6.3.1 SYNTHESIS OF (S)-2-FERROCENYL-4-(L-METHYLETHYL)OXAZOLINE 46
2.6.3.2 SYNTHESIS OF (S,S ; ,)-2-[2-(DIPHENYLPHOSPHINO)FERROCENYL]-4-
(1-METHYLETHYL) OXAZOLINE 47 2.6.4 SYNTHESIS OF (S P
)-N,N-DIISOPROPYL-2-(DIPHENYLPHOSPHINO)
FERROCENECARBOXAMIDE 48 2.6.4.1 (S P
)-N,N-DIISOPROPYL-2-(DIPHENYLPHOSPHINO) FERROCENECARBOXAMIDE 48
REFERENCES 49
3 MONODENTATE CHIRAL FERROCENYL LIGANDS 55 JI-BAO XIA, TIMOTHY
F.JAMISON, AND SHU-LI YOU 3.1 INTRODUCTION 55
3.2 NICKEL-CATALYZED ASYMMETRIE REDUCTIVE COUPLING REACTIONS 55 3.2.1
SYNTHESIS OF P-CHIRAL, MONODENTATE FERROCENYL PHOSPHINES 56 3.2.2
NICKEL-CATALYZED ASYMMETRIE REDUCTIVE COUPLING OF ALKYNES AND ALDEHYDES
56 3.2.3 NICKEL-CATALYZED ASYMMETRIE REDUCTIVE COUPLING OF ALKYNES
AND KETONES 60
3.2.4 NICKEL-CATALYZED ASYMMETRIE THREE-COMPONENT COUPLING OF ALKYNES,
IMINES, AND ORGANOBORON REAGENTS 61 3.3 COPPER(I)-CATALYZED ASYMMETRIE
ALLYLIC ALKYLATION REACTIONS 62 3.4 ASYMMETRIE SUZUKI-MIYAURA REACTIONS
64 3.5 ADDITION OF ORGANOALUMINUM TO ALDEHYDES AND ENONES 65
3.6 ASYMMETRIE NUCLEOPHILIC CATALYSIS 66 3.7 CONCLUSION AND PERSPECTIVES
70
REFERENCES 70
4 BIDENTATE 1,2-FERROCENYL DIPHOSPHINE LIGANDS 73 HANS-ULRICH BLASER AND
MATTHIAS LOTZ 4.1 INTRODUCTION 73
4.2 TYPE A BOTH PR 2 GRAUPS ATTACHED TO THE CP RING 74 4.3 TYPE B ONE PR
2 GROUP ATTACHED TO THE CP RING, ONE PR 2 GROUP ATTACHED TO THE
^-POSITION OF THE SIDE CHAIN 75
IMAGE 3
CONTENTS VII
4.3.1 JOSIPHOS 76
4.3.2 IMMOBILIZED JOSIPHOS 80 4.3.3 JOSIPHOS ANALOGS 82
4.4 TYPE C ONE PR 2 GROUP ATTACHED TO THE CP RING, ONE PR 2 GROUP
ATTACHED TO THE SS-POSITION OF THE SIDE CHAIN 83
4.4.1 BOPHOZ AND ANALOGS 83 4.5 TYPE D, ONE PR 2 GROUP ATTACHED TO THE
CP RING, ONE PR 2 GROUP ATTACHED TO OTHER POSITIONS OF THE SIDE CHAIN 85
4.5.1 TANIAPHOS 86
4.6 TYPE E, BOTH PR 2 GROUPS ATTACHED TO SIDE CHAINS 87 4.6.1 WALPHOS 88
4.6.2 TRAP 90
REFERENCES 91
5 1,2-P,N-BIDENTATE FERROCENYL LIGANDS 97 YONG GUT ZHOU AND XUE LONG HOU
5.1 INTRODUCTION 97
5.2 ASYMMETRIE HYDROGENATION AND ASYMMETRIE TRANSFER HYDROGENATION 97
5.2.1 ASYMMETRIE HYDROGENATION 97 5.2.1.1 ASYMMETRIE HYDROGENATION OF
ALKENES 98 5.2.1.2 ASYMMETRIE HYDROGENATION OF KETONES 101 5.2.1.3
ASYMMETRIE HYDROGENATION OF HETEROAROMATIC COMPOUNDS 103 5.2.1.4
ASYMMETRIE HYDROGENATION OF IMINES 104
5.2.2 ASYMMETRIE TRANSFER HYDROGENATION 106 5.2.3 ASYMMETRIE
HYDROSILYLATION REACTION 709 5.2.3.1 PALLADIUM-CATALYZED ASYMMETRIE
HYDROSILYLATION OFC=CBOND 110
5.2.3.2 ASYMMETRIE HYDROSILYLATION OF A C~O BOND 112 5.2.3.3 ASYMMETRIE
HYDROSILYLATION OF THE C=N BOND 117 5.2.4 ASYMMETRIE HYDROBORATION 118
5.3 FORMATION OF A C-C BOND 121
5.3.1 PD-CATALYZED ASYMMETRIE ALLYLIC SUBSTITUTION REACTION 121 5.3.2
ASYMMETRIE HECK REACTION AND CROSS-COUPLING REACTIONS 126 5.3.3 ADDITION
OF ORGANOMETALLIC REAGENTS TO A C=X BOND 129 5.4 CYCLOADDITION REACTIONS
132 5.4.1 [3 + 2] CYCLOADDITION REACTIONS 132
5.4.2 ASYMMETRIE CYCLOPROPANATION REACTIONS 136 5.4.3 ASYMMETRIE
DIELS-ALDER REACTIONS 136 5.5 MISCELLANEOUS REACTIONS 137 5.6 CONCLUSION
AND PERSPECTIVES 140 5.7 EXPERIMENTAL: SELECTED PROCEDURES 140
5.7.1 UGI'S AMINE SYNTHESIS 140 5.7.1.1 SYNTHESIS OF
A-FERROCENYLETHYLDIMETHYLAMINE (2} 141 5.7.1.2 RESOLUTION OF 2 141
IMAGE 4
VIII CONTENTS
5.7.1.3
5.7.2
5.7.2.1 5.7.2.2 5.7.2.3
SYNTHESIS OF (S)-N, JV-DIMETHYL-L-[(.R)-2-(DIPHENYLPHOSPHINO)
FERROCENYL]ETHYLAMINE 141 (S, S P )-2-[(S)-2
-(DIPHENYLPHOSPHINO)FERROCENYL]-4-(L-METHYLETHYL) OXAZOLINE 142
SYNTHESIS OF (2S)-JV-(L-HYDROXY-3-METHYLBUTYL)FERROCENARNIDE 142
SYNTHESIS OF FERROCENYLOXAZOLINE 142 SYNTHESIS OF (S, S P
)-2-[(S)-2-(DIPHENYIPHOSPHINO)FERROCENYL]-4- (1 -METHYLETHYL) OXAZOLINE
143 REFERENCES 144
6 N,O-BIDENTATE FERROCENYL LIGANDS 149 ANNE NIJS, OLGA GARCIA MANCHENO,
AND CARSTEN BOIM 6.1 INTRODUCTIORT 149
6.2 ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES 149 6.2.1 ADDITION OF
DIALKYLZINC 150 6.2.1.1 WITH FERROCENYL AMINO ALCOHOLS 150 6.2.1.2 WITH
FERROCENYL OXAZOLMYL ALCOHOLS 158
6.2.1.3 WITH AZAFERROCENES 160 6.2.2 ADDITION OF ARYLZINC 161 6.2.3
ADDITION OF PHENYLACETYLENE 165 6.3 ADDITION TO ALDEHYDES WITH BORON
REAGENTS 165 6.3.1 ARYL TRANSFERS WITH BORONIC ESTERS 165 6.3.2 ARYL
TRANSFER WITH TRIPHENYLBORANE [PH 3 B] 166
6.3.3 BORONIC ACIDS AS ARYL SOURCE 167 6.3.4 ALKENYLBORONIC ACIDS IN
ALKENYL TRANSFER REACTIONS 168 6.4 OTHER TRANSFORMATIONS: ASYMMETRIE
EPOXIDATION 168
6.5 CONCLUSION AND PERSPECTIVES 169 6.6 EXPERIMENTAL: SELECTED
PROCEDURES 170 6.6.1 ADDITION OF DIETHYLZINC TO BENZALDEHYDE WITH
FERROCENE 13 170 6.6.2 PHENYLACETYLENE ADDITION TO ALDEHYDES WITH
FERROCENE 24 170
6.6.3 PHENYL TRANSFER (ZNET2 + ZNPH 2 ) TO ALDEHYDES WITH FERROCENE 13
6.6.4 PHENYL TRANSFER TO ALDEHYDES WITH TRIPHENYLBORANE ON A GRAM SCALE
171 6.6.5 ARYL TRANSFER TO ALDEHYDES WITH BORONIC ACIDS ON A MULTIGRAM
SCALE 171 REFERENCES 173
7 SYMMETRICAL L,V-BIDENTATE FERROCENYL LIGANDS 175 WONBIN ZHANG AND
DELONG LIU 7.1 INTRODUCTION 175
7.2 SYMMETRICAL L,L'-DISUBSTITUTED FERROCENYL LIGANDS 177 7.2.1
P-CENTERED CHIRAL DIPHOSPHINE LIGANDS 177 7.2.2 C-CENTERED CHIRAL
DIPHOSPHINE LIGANDS 180
7.2.3 CHIRAL NITROGEN-CONTAINING LIGANDS 188 7.3 SYMMETRICAL
L,L',2,2'-TETRASUBSTITUTED FERROCENYL LIGANDS 193
171
IMAGE 5
CONTENTS IX
7.3.1 TETRASUBSTITUTED FERROCENYL DIPHOSPHINE LIGANDS WITH
MULTI-CHIRALITIES 193 7.3.2 TETRASUBSTITUTED FERROCENYL LIGANDS WITH
ONLY PLANAR CHIRALITY 198 7.3.3 OTHER TETRASUBSTITUTED FERROCENYL
LIGANDS 201 7A ANALOGS OF FERROCENES: SYMMETRICAL L,L'-BIDENTATE
RUTHENOCENYL LIGANDS 203 7.5 CONCLUSION AND PERSPECTIVES 208 7.6
EXPERIMENTAL: SELECTED PROCEDURES 208 7.6.1 TYPICAL PROCEDURE FOR THE
PREPARATION OF
FERROCENYLDIPHOSPHINES L-2 208 7.6.2 TYPICAL PROCEDURE FOR THE
PREPARATION OF THE {R,.R)-FERROCENYL DIOL 14 208 7.6.3 TYPICAL PROCEDURE
FOR THE PREPARATION OF (AR,A'R)-2,2'-
BIS(A-N,N-DIMETHYLAMINOPROPYL)-(S,S}-L,L'-
BIS(DIPHENYLPHOSPHMO)FERROCENE L-17C 209 7.6.4 TYPICAL PROCEDURE FOR THE
PREPARATION OF C 2 -SYMMETRIE L,L',2,2'-TETRASUBSTITUTED FERROCENE
DERIVATIVES L-18 209 7.6.5 TYPICAL PROCEDURE FOR THE PREPARATION OF THE
FERROCENE-BASED
ESTER AMIDE 59 209 7.6.6 TYPICAL PROCEDURE FOR THE PREPARATION OF
(-)-(S)-(S)4,L'-
BISTDIPHENYLPHOSPHINOL^^'-BIS-TMETHOXYCARBONYLLFERROCENEL^L 210 7.6.7
TYPICAL PROCEDURE FOR THE PREPARATION OF 1 ,L'-BIS[(S)-4-
ISOPROPYLOXAZOLIN-2-YL]-RUTHENOCENE 82 210 REFERENCES 211
8 UNSYMMETRICAL 1,1-BIDENTATE FERROCENYL LIGANDS 215 SHU-LI YOU 8.1
INTRODUCTION 215
8.2 PALLADIUM-CATALYZED ASYMMETRIE ALLYLIC SUBSTITUTION REACTION 215
8.2.1 A MODEL REACTION OF SYMMETRICAL 1,3-DISUBSTITUTED 2-PROPENYL
ACETATES 216 8.2.2 SUBSTRATE VARIANTS OF PALLADIUM-CATALYZED ASYMMETRIE
ALLYLIC SUBSTITUTION REACTION 221 8.2.3 REGIOSELECTIVE CONTROL FOR
UNSYMMETRICAL ALLYLIC ACETATES 224 8.2.4 APPLICATIONS OF
PALLADIUM-CATALYZED ASYMMETRIE ALLYLIC SUBSTITUTION REACTION 228 8.3
GOLD OR SUEVER-CATALYZED ASYMMETRIE ALDOL REACTIONS 229 8.3.1
GOLD-CATALYZED ASYMMETRIE ALDOL REACTIONS 229 8.3.2 SILVER-CATALYZED
ASYMMETRIE ALDOL REACTIONS 232 8.3.3 APPLICATIONS OF GOLD OR
SILVER-CATALYZED ASYMMETRIE
ALDOL REACTIONS 232 8.4 ASYMMETRIE HYDROGENATION 234 8.4.1 RH-CATALYZED
HYDROSILYLATION 234 8.4.2 RH, IR, RU-CATALYZED HYDROGENATION 235 8.4.3
RH-CATALYZED HYDROBORATION 238
IMAGE 6
X
CONTENTS
8.5 8.5 8.5 8.5
8.6 8.6 8.6 8.7
1 2 3
1 2
8.7.1 8.7 8.7 2
3
8.7.4 8.7 8.8
8.9 8.9 8.9
5
L
2
ASYMMETRIE CROSS-COUPLING REACTION 239 NICKEL-CATALYZED KUMADA COUPLING
REACTION 239 PALLADIUM-CATALYZED CROSS-COUPLING REACTION 240
PALLADIUM-CATALYZED SUZUKI-MIYAURA REACTION AND CE-ARYLATION OFAMIDES
241 ASYMMETRIE HECK REACTION 242
INTRAMOLECULAR HECK REACTION 242 INTERMOLECULAR HECK REACTION 243
MISCELLANEOUS 244
ADDITION OF ZINC REAGENT TO ALDEHYDES 244 CONJUGATE ADDITION 247
RH-CATALYZED RING OPENING REACTION OF OXABENZONORBORNADIENE 247
ASYMMETRIE CYCLOPROPANATION OF ALKENES WITH DIAZO ESTERS 248 ASYMMETRIE
PALLADIUM-CATALYZED HYDROESTERIHCATION OF STYRENE 249
CONCLUSION AND PERSPECTIVES 250 EXPERIMENTAL: SELECTED PROCEDURES 250
SYNTHESIS OF COMPOUND (S,SP)-L4D FROM (S)-5A 250 SYNTHESIS OF COMPOUND
{S,R PH0S ,R)-H8D AND (S,S PHOS ,R)-L&D
FROM (S)-5D 251 REFERENCES 253
9 SULFUR- AND SELENI'UM-CONTAINING FERROCENYL LIGANDS 257 JUAN C.
CARRETERO, JAVIER ADRIO, AND MARIA RODRIGUEZ RIVERO
9.1 INTRODUCTION 257
9.2 ASYMMETRIE ALLYLIC SUBSTITUTION 258 9.2.1 PALLADIUM-CATALYZED
ALLYLIC SUBSTITUTION 258 9.2.1.1 BIDENTATE N,S-FERROCENE LIGANDS 259
9.2.1.2 BIDENTATE P T S-FERROCENE LIGANDS 260 9.2.2 COPPER-CATALYZED
ALLYLIC SUBSTITUTION 265 9.3 OTHER ASYMMETRIE PALLADIUM-CATALYZED
REACTIONS 266 9.3.1 ASYMMETRIE HECK REACTIONS 266 9.3.2 DESYMMETRIZATION
OF HETEROBICYCLIC ALKENES 267
9.4 GOLD-CATALYZED REACTIONS 268 9.5 ASYMMETRIE REDUETIONS 269
9.6 ASYMMETRIE 1,2- AND 1,4-NUCLEOPHILIC ADDITION 270 9.6.1 ASYMMETRIE
1,2 ADDITION TO ALDEHYDES AND IMINES 270 9.6.2 ASYMMETRIE 1,4-CONJUGATE
ADDITION 272 9.7 ASYMMETRIE CYCLOADDITION REACTIONS 272
9.7.1 [4 + 2] CYCLOADDITIONS 272 9.7.2 [3 + 2] CYCLOADDITIONS 274
9.8 ASYMMETRIE NUCLEOPHILIC CATALYSIS 276 9.9 CONCLUSION AND
PERSPECTIVES 277
9.10 EXPERIMENTAL: SELECTED PROCEDURES 278 9.10.1 PALLADIUM-CATALYZED
ALLYLIC ALKYLATION REACTION WITH LIGAND 3A 278
IMAGE 7
CONTENTS
9.10.2 FESULPHOS/PALLADIUM-CATALYZED ASYMMETRIE RING OPENING OF
BICYCLIC ALKENES 278 9.10.3 RHODIUM-CATALYZED HYDROGENATION
OT-(N-ACETAMIDO)ACRYLATE IN THE PRESENCE OF LIGAND 20 278 9.10.4
CU-FESULPHOS CATALYZED FORMAL AZA DIELS-ALDER REACTIONS OF
N-SULFONYL IMINES 278 REFERENCES 280
10 BIFERROCENE LIGANDS 283
RYOICHI KUWANO
10.1 INTRODUCTION 283
10.2 TRANS-CHELATING CHIRAL BISPHOSPHINES: TRAP 284 10.2.1 SYNTHESIS OF
TRAP 285 10.2.2 METAL COMPLEXES OF TRAP 286 10.2.3 ASYMMETRIE REACTIONS
OF 2-CYANOCARBOXYLATES 287 10.2.4 ASYMMETRIE HYDROSILYLATION OF KETONES
291 10.2.5 ASYMMETRIE HYDROGENATION OF OLEFMS 292 10.2.6 ASYMMETRIE
HYDROGENATIONS OF HETEROAROMATICS 296
10.2.7 MISCELLANEOUS REACTIONS USING TRAP 298 10.3
2,2-BIS(DIARYLPHOSPHINO)-L,L-BIFERROCENES: BIFEP 299 10.4 MISCELLANEOUS
BIFERROCENE-BASED CHIRAL LIGANDS 302 10.5 CONCLUSION 303
REFERENCES 304
11 APPLICATIONS OF AZA- AND PHOSPHAFERROCENES AND RELATED COMPOUNDS IN
ASYMMETRIE CATALYSIS 307 NICOLOS MARION AND GREGORY C. FU 11.1
INTRODUCTION 307
11.2 BACKGROUND ON AZA- AND PHOSPHAFERROCENES 308 11.2.1 AZAFERROCENES
308 11.2.2 PHOSPHAFERROCENES 309 11.3 AZAFERROCENES IN CATALYSIS 310
11.3.1 NUCLEOPHILK CATALYSIS 310 11.3.1.1 ACYLATIONS 310
11.3.1.2 HALOGENATIONS 316
11.3.1.3 CYCLOADDITIONS 317 11.3.1.4 NUCLEOPHILIC ADDITIONS TO CARBONYL
GROUPS 319 11.3.2 TRANSIUEON-METAL CATALYSIS 319 11.3.2.1
COPPER-CATALYZED CYCLOPROPANATIONS OF OLEFINS 319 11.3.2.2
COPPER-CATALYZED INSERTIONS OF DIAZO COMPOUNDS 320 11.3.2.3
COPPER-CATALYZED CYCLOADDITIONS 322 11.3.2.4 OLEFIN POLYMERIZATIONS 322
11.3.2.5 RHODIUM-CATALYZED REDUCTIONS OF KETONES 324 11.4
PHOSPHAFERROCENES IN CATALYSIS 324 11.4.1 REDUETION REACTIONS 325
IMAGE 8
XII CONTENTS
11.4.2 PALLADIUM-CATALYZED ALLYLIC ALKYLATIONS 326
11.4.3 RHODIUM-CATALYZED ISOMERIZATIONS 328 11.4.4 COPPER-CATALYZED
CONJUGATE ADDITIONS 328 11.4.5 COPPER-CATALYZED CYCLOADDITIONS 329
11.4.6 PALLADIUM-CATALYZED CROSS-COUPLINGS 331 11.5 CONCLUSIONS 333
REFERENCES 333
12 METALLOCYCLIC FERROCENYL LIGANDS 337 CHRISTOPHERJ. RICHARDS 12.1
INTRODUCTION 337
12.2 ASYMMETRIE SYNTIIESIS OF PLANAR CHIRAL METALLOCYCLIC COMPLEXES 339
12.2.1 RESOLUTION 341 12.2.2 DIASTEREOTOPIC C-H ACTIVATION 342 12.2.3
OXIDATIVE ADDITION OF PALLADIUM(O) 348 12.2.4 TRANS METALATION 350
12.2.5 ENANTIOSELECTIVE PALLADATION 352 12.3 STOICHIOMETRIC SYNTHETIC
APPLICATIONS OF SCALEMIC PLANAR CHIRAL METALLOCYCLIC COMPLEXES 354 12.3J
PHOSPHINE RECOGNITION 354 12.3.2 GENERATION OF PLANAR CHIRAL FERROCENE
DERIVATIVES BY M-C BOND
CLEAVAGE 354
12.4 ASYMMETRIE CATALYSIS WITH SCALEMIC PLANAR CHIRAL PALLADOCYCLIC
COMPLEXES 355 12.4.1 ALLYLIC IMIDATE REARRANGEMENT 356 12.4.2
INTRAMOLECULAR AMINOPALLADATION 363 12.5 CONCLUSION 364
REFERENCES 364
A SHOW CASE OF THE MOST EFFECTIVE CHIRAL FERROCENE LIGANDS IN VARIOUS
CATALYTIC REACTIONS 369 A.1 ASYMMETRIE ALLYLIC SUBSTITUTION REACTIONS
369 A.L.L COPPER(I)-CATALYZED ASYMMETRIE ALLYLIC ALKYLATION REACTIONS
369
A.1.2 PALLADIUM-CATALYZED ASYMMETRIE ALLYLIC SUBSTITUTION REACTIONS 370
A.L.2.1 ALKYLATION 370 A.1.2.2 AMINATION 371 A.1.3 GENERATING 7T-ALLYL
PALLADIUM COMPLEX THROUGH THE REACTION OF
ALLENE WITH LODOBENZENE 372 A.1.4 REGIOSELECTIVE CONTROL CONCERNED WITH
UNSYMMETRICALLY 1,3-DISUBSTITUTED 2-PROPENYL ACETATE 372 A. 1.4.1 REGIO-
AND ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC
SUBSTITUTION 372
A.L.4.2 ALLYLIC SUBSTITUTION OF 2-CYANOPROPIONATE 373 A.L.4.3 ALLYLIC
SUBSTITUTION OF THE CONJUGATED DIENYL ACETATES 373
IMAGE 9
CONTENTS XIII
A.L.4.4 ALLYLIC SUBSTITUTION WITH ACYCLIC KETONE ENOLATE AS NUCLEOPHILE
374
A.L.4.5 ALLYLIC ALKYLATION WITH N,N-DISUBSTITUTED AMIDES AS NUCLEOPHILE
374 A.L.4.6 ALLYLIC ALKYLATION WITH ACTIVATED CYCLIC KETONE AS
NUCLEOPHILE 374 A.1.5 APPLICATIONS OF PALLADIUM-CATALYZED ASYMMETRIE
ALLYLIC SUBSTITUTION REACTION 375
A.2 ASYMMETRIE ALDOL REACTIONS 375 A.2.1 GOLD-CATALYZED ASYMMETRIE ALDOL
REACTIONS 375 A.2.1.1 ALDEHYDE WITH ISOCYANOACETATE 375 A.2.1.2 IMINES
WITH ISOCYANOACETATE 376
A.2.2 SILVER-CATALYZED ASYMMETRIE ALDOL REACTIONS 376 A.2.3 APPLICATIONS
OF GOLD OR SILVER-CATALYZED ASYMMETRIE ALDOL REACTIONS 376 A.3
ASYMMETRIE CYCLOADDITION REACTIONS 377 A.3.1 [3 + 2] CYCLOADDITION
REACTIONS 377 A.3.2 [4 + 2] CYCLOADDITION REACTIONS 377 A.3.3 [3 F 2]
CYCLOADDITION REACTIONS 378 A.3.4 ASYMMETRIE 1,3-DIPOLAR CYCLOADDITION
OF AZOMETHINE YLIDES
WITH N-PHENYL MALEIMIDE 378 A.3.5 [3 - 2] CYCLOADDITION OF ALKYNES WITH
AZOMETHINE IMINES 378 A.4 ASYMMETRIE HYDROGENATION 379 A.4.1 ASYMMETRIE
HYDROGENATION OF ALKENES (C=C) 379
A.4.1.1 ASYMMETRIE HYDROGENATION OF UNFUNCTIONALIZED ALKENES 379 A.4.1.2
ASYMMETRIE HYDROGENATION OF CC,SS-UNSATURATED ESTERS 379 A.4.1.3
HYDROGENATION OF DEHYDRO C-AMINO ACID 380
A.4.1.4 ASYMMETRIE HYDROGENATION OF ACTIVATED IMINE C=N BOND 380 A.4.1.5
APPLICATIONS: HYDROGENATION OF A,SS-UNSATURATED ACID 381 A.4.1.6
ASYMMETRIE HYDROGENATION OF ALKYL A-ACETAMIDO ACRYLATES 381 A.4.1. 7
INDUSTRIAL APPLICATIONS 382
A.4.2 ASYMMETRIE HYDROGENATION OF ALKENES (OR C=N) 383 A.4.2.1
IR-CATALYZED ASYMMETRIE HYDROGENATION OF QUINOLINES 383 A.4.2.2
INDUSTRIAL APPLICATIONS 384
A.4.3 ASYMMETRIE HYDROGENATION OF KETONES (C-O) 384 A.4.3.1 ASYMMETRIE
HYDROGENATION OF ACETOPHENONE 384 A.4.3.2 ASYMMETRIE HYDROGENATION OF
SS-AMINOKETONE 385 A.4.4 ASYMMETRIE HYDROBORATION 385
A.4.5 ASYMMETRIE HYDROSILYLATION REACTION 385 A.4.6 ASYMMETRIE TRANSFER
HYDROGENATION 386 A.5 PD-CATALYZED ASYMMETRIE HECK REACTION 386 A.6
ADDITION OF ORGANOZINC REAGENTS 387
A.6.1 ADDITION OF DIALLCYLZINC TO ALDEHYDES 387 A.6.2 ADDITION OF
DIARYLZINC TO ALDEHYDES 388 A.6.3 ADDITION OF DIALKYLZINC TO C=N BOND
388
A.6.4 ADDITION OF PHENYLACETYLENE TO ALDEHYDES 389 A.6.5 ADDITION TO
ALDEHYDES WITH BORON REAGENTS 389 A.6.5.1 ARYL TRANSFER WITH BORONIC
ESTER 389
IMAGE 10
XIV CONTENTS
A.6.5.2 ARYL TRANSFER WITH TRIPHENYLBORANE 389
A.6.5.3 ARYL TRANSFER WITH BORONIC ACIDS 390 A.7 ASYMMETRIE
REARRANGEMENT OF ALLYLIC IMIDATES 390 A.7.1 REARRANGEMENT OF
N-ARYLBENZIMIDATES 390 A.7.2 REARRANGEMENT OF N-ARYL-TRIFLUORACETIMIDATE
390 A.7.3 REARRANGEMENT WITH ADDED NUCLEOPHILES 391 A.8 CU-CATALYZED
CYCLOPROPANATION 391 A.8.1 WITH DIPHENYLETHENE 391 A.S.2 WITH ARYL,
ALKYL OR SILYLETHENE 3 91 A.9 COUPLING REACTION OF VINYL BROMIDE AND
L-PHENYLETHYLZINC
CHLORIDE 392
A.10 ENANTIOSELECTIVE INTRAMOLECULAR AMINOPALLADATION 392 A.11
NICKEL-CATALYZED ASYMMETRIE THREE-COMPONENT COUPLING OF ALKYNES, IMINES,
AND ORGANOBORON REAGENTS 392 AM REACTIONS WITH KETENES 393
A.12.1 O-ACYLATION WITH KETENES 393 A.12.2 KINETIC RESOLUTION BY
O-ACYLATION 393 A.12.3 N-ACYLATION WITH KETENES 394 A.12.4 KINETIC
RESOLUTION BY N-ACYLATION 394 A.12.5 C-ACYLATION VIA REARRANGEMENT 394
A.12.6 CYDOADDITIONS 395 A.12.7 COPPER-CATALYZED INSERTIONS OF DIAZO
COMPOUNDS 395 A.12.8 COPPER-CATALYZED CYDOADDITIONS 395 A.13 RING
OPENING REACTION 396
A.13.1 DESYMMETRIZATION BY HALOGENATIONS 396 A.13.2 RING OPENING OF
BICYCLIC ALKENES 396
INDEX 397 |
| any_adam_object | 1 |
| author_GND | (DE-588)140148124 |
| building | Verbundindex |
| bvnumber | BV036041114 |
| callnumber-first | Q - Science |
| callnumber-label | QD412 |
| callnumber-raw | QD412.F4 |
| callnumber-search | QD412.F4 |
| callnumber-sort | QD 3412 F4 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VE 7040 VH 9700 VK 5500 |
| classification_tum | CHE 624f CHE 330f CHE 167f |
| ctrlnum | (OCoLC)496229347 (DE-599)DNB991678761 |
| dewey-full | 547.05621 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.05621 |
| dewey-search | 547.05621 |
| dewey-sort | 3547.05621 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Physik Chemie |
| format | Book |
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| id | DE-604.BV036041114 |
| illustrated | Illustrated |
| indexdate | 2024-09-25T18:00:12Z |
| institution | BVB |
| isbn | 9783527322800 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-018932982 |
| oclc_num | 496229347 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-91G DE-BY-TUM DE-11 DE-19 DE-BY-UBM |
| physical | XVII, 414 S. graph. Darst. 25 cm |
| publishDate | 2010 |
| publishDateSearch | 2010 |
| publishDateSort | 2010 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Chiral ferrocenes in asymmetric catalysis synthesis and applications ed. by Li-Xin Dai ... Weinheim Wiley-VCH 2010 XVII, 414 S. graph. Darst. 25 cm txt rdacontent n rdamedia nc rdacarrier Literaturangaben Asymmetric synthesis Catalysis Chirality Ferrocene Katalyse (DE-588)4029921-1 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Chirale Verbindungen (DE-588)4348527-3 gnd rswk-swf Ferrocenderivate (DE-588)4154117-0 gnd rswk-swf Ferrocenderivate (DE-588)4154117-0 s Chirale Verbindungen (DE-588)4348527-3 s Asymmetrische Synthese (DE-588)4135603-2 s Katalyse (DE-588)4029921-1 s DE-604 Dai, Lixin 1924-2024 Sonstige (DE-588)140148124 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3192440&prov=M&dok_var=1&dok_ext=htm Inhaltstext OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018932982&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Chiral ferrocenes in asymmetric catalysis synthesis and applications Asymmetric synthesis Catalysis Chirality Ferrocene Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd Ferrocenderivate (DE-588)4154117-0 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4135603-2 (DE-588)4348527-3 (DE-588)4154117-0 |
| title | Chiral ferrocenes in asymmetric catalysis synthesis and applications |
| title_auth | Chiral ferrocenes in asymmetric catalysis synthesis and applications |
| title_exact_search | Chiral ferrocenes in asymmetric catalysis synthesis and applications |
| title_full | Chiral ferrocenes in asymmetric catalysis synthesis and applications ed. by Li-Xin Dai ... |
| title_fullStr | Chiral ferrocenes in asymmetric catalysis synthesis and applications ed. by Li-Xin Dai ... |
| title_full_unstemmed | Chiral ferrocenes in asymmetric catalysis synthesis and applications ed. by Li-Xin Dai ... |
| title_short | Chiral ferrocenes in asymmetric catalysis |
| title_sort | chiral ferrocenes in asymmetric catalysis synthesis and applications |
| title_sub | synthesis and applications |
| topic | Asymmetric synthesis Catalysis Chirality Ferrocene Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd Ferrocenderivate (DE-588)4154117-0 gnd |
| topic_facet | Asymmetric synthesis Catalysis Chirality Ferrocene Katalyse Asymmetrische Synthese Chirale Verbindungen Ferrocenderivate |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3192440&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=018932982&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT dailixin chiralferrocenesinasymmetriccatalysissynthesisandapplications |