Axially chiral compounds: asymmetric synthesis and applications
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| Sprache: | English |
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Weinheim
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[2021]
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| Beschreibung: | xiv, 322 Seiten Illustrationen 24.4 cm x 17 cm |
| ISBN: | 9783527347124 3527347127 |
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MARC
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| 020 | |a 9783527347124 |c hbk. |9 978-3-527-34712-4 | ||
| 020 | |a 3527347127 |9 3-527-34712-7 | ||
| 024 | 3 | |a 9783527347124 | |
| 035 | |a (OCoLC)1284997448 | ||
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| 040 | |a DE-604 |b ger |e rda | ||
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| 084 | |a VK 5800 |0 (DE-625)147412:253 |2 rvk | ||
| 084 | |a 540 |2 23sdnb | ||
| 245 | 1 | 0 | |a Axially chiral compounds |b asymmetric synthesis and applications |c edited by Tan Bin |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c [2021] | |
| 264 | 4 | |c © 2021 | |
| 300 | |a xiv, 322 Seiten |b Illustrationen |c 24.4 cm x 17 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Axiale Chiralität |0 (DE-588)4766198-7 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Chirale Verbindungen |0 (DE-588)4348527-3 |2 gnd |9 rswk-swf |
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Homogene Katalyse | ||
| 653 | |a Homogeneous Catalysis | ||
| 653 | |a Methods - Synthesis & Techniques | ||
| 653 | |a Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 653 | |a Physical Chemistry | ||
| 653 | |a Physikalische Chemie | ||
| 653 | |a CH42: Homogene Katalyse | ||
| 653 | |a CH81: Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 653 | |a CH90: Physikalische Chemie | ||
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Chirale Verbindungen |0 (DE-588)4348527-3 |D s |
| 689 | 0 | 1 | |a Axiale Chiralität |0 (DE-588)4766198-7 |D s |
| 689 | 0 | 2 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Tan, Bin |0 (DE-588)1244775401 |4 edt | |
| 710 | 2 | |a Wiley-VCH |0 (DE-588)16179388-5 |4 pbl | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-82518-9 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-82516-5 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, OBOOK |z 978-3-527-82517-2 |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032883134&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-032883134 | ||
Datensatz im Suchindex
| _version_ | 1804182800731996160 |
|---|---|
| adam_text | V
CONTENTS
PREFACE
XIII
PART
I
ASYMMETRIC
SYNTHESIS
1
1
INTRODUCTION
AND
CHARACTERISTICS
3
YONG-BIN
WANG,
SHAO-HUA
XIANG,
AND
BIN
TAN
1.1
INTRODUCTION
AND
CLASSIFICATION
3
1.2
SPECIFICATION
OF
CONFIGURATION
9
REFERENCES
11
2
METAL-CATALYZED
ASYMMETRIC
SYNTHESIS
OF
BIARYL
ATROPISOMERS
13
TAO
ZHOU
AND
BING-FENG
SHI
2.1
INTRODUCTION
13
2.2
BIARYL
COUPLING
13
2.2.1
CROSS-COUPLING
13
2.2.1.1
KUMADA-TAMAO-CORRIU
CROSS-COUPLING
14
2.2.1.2
NEGISHI
CROSS-COUPLING
15
2.2.1.3
SUZUKI-MIYAURA
CROSS-COUPLING
15
2.2.2
OTHER
TYPES
OF
CROSS-COUPLING
24
2.2.3
OXIDATIVE
COUPLING
24
2.2.3.1
CU-CATALYZED
OXIDATIVE
COUPLING
25
2.2.3.2
OXIDATIVE
COUPLING
REACTIONS
WITH
OTHER
METALS
27
2.3
DESYMMETRIZATION
AND
(DYNAMIC)
KINETIC
RESOLUTION
VIA
FUNCTIONAL
GROUP
TRANSFORMATION
29
2.3.1
DESYMMETRIZATION
OF
PROCHIRAL
BIARYLS
29
2.3.2
KINETIC
RESOLUTION
OF
RACEMIC
AXIALLY
CHIRAL
BIARYLS
30
2.3.3
DYNAMIC
KINETIC
RESOLUTION
OF
RACEMIC
AXIALLY
CHIRAL
BIARYLS
30
2.3.4
RING-OPENING
REACTIONS
32
2.4
FORMATION
OF
AROMATIC
RING
VIA
[2
+
2
+
2]
CYCLOADDITION
35
2.4.1
COBALT-CATALYZED
ENANTIOSELECTIVE
[2
+
2
+
2]
CYCLOADDITIONS
35
2.4.2
RHODIUM-CATALYZED
ENANTIOSELECTIVE
[2
+
2
+
2]
CYCLOADDITIONS
36
VI
CONTENTS
2.4.3
IRIDIUM-CATALYZED
ENANTIOSELECTIVE
[2
+
2
+
2]
CYCLOADDITIONS
36
2.5
C
-
H
BOND
FUNCTIONALIZATION
38
2.5.1
CHIRAL
CATALYST-CONTROLLED
C
-
H
BOND
FUNCTIONALIZATION
38
2.5.2
CHIRAL
AUXILIARY-INDUCED
C
-
H
BOND
FUNCTIONALIZATION
40
2.5.3
ATROPOSELECTIVE
C
-
H
ARYLATION
40
2.6
SUMMARY
AND
CONCLUSIONS
42
REFERENCES
42
3
ORGANOCATALYTIC
ASYMMETRIC
SYNTHESIS
OF
BIARYL
ATROPISOMERS
47
SHAOYU
LI,
SHAO-HUA
XIANG,
AND
BIN
TAN
3.1
INTRODUCTION
47
3.2
ATROPOSELECTIVE
SYNTHESIS
OF
BIARYLS
BY
KINETIC
RESOLUTION
STRATEGY
47
3.2.1
CONVENTIONAL
KINETIC
RESOLUTION
47
3.2.1.1
KINETIC
RESOLUTION
VIA
ASYMMETRIC
ALKYLATION
48
3.2.1.2
KINETIC
RESOLUTION
VIA
ASYMMETRIC
ACYLATION
50
3.2.1.3
KINETIC
RESOLUTION
VIA
ASYMMETRIC
TRANSFER
HYDROGENATION
AND
MICHAEL
ADDITION
53
3.2.2
DYNAMIC
KINETIC
RESOLUTION
STRATEGY
54
3.2.2.1
DKR
VIA
ASYMMETRIC
ELECTROPHILIC
BROMINATION
54
3.2.2.2
DKR
VIA
ASYMMETRIC
NUCLEOPHILIC
ADDITION
56
3.2.2.3
DKR
BASED
ON
ASYMMETRIC
RING-OPENING/EXPANSION
TRANSFORMATION
57
3.3
ATROPOSELECTIVE
SYNTHESIS
OF
BIARYLS
BY
DESYMMETRIZATION
STRATEGY
59
3.4
ATROPOSELECTIVE
ARENE
FORMATION
TO
ACCESS
AXIALLY
CHIRAL
BIARYLS
61
3.4.1
INTRAMOLECULAR
ATROPOSELECTIVE
ARENE
FORMATION
61
3.4.2
ATROPOSELECTIVE
ARENE
FORMATION
VIA
INTERMOLECULAR
ANNULATION
63
3.5
ATROPOSELECTIVE
SYNTHESIS
OF
BIARYLS
VIA
DIRECT
C-H
ARYLATION
STRATEGY
67
3.5.1
ORGANOCATALYTIC
C-H
ARYLATION
BY
[3,3]-SIGMATROPIC
REARRANGEMENT
67
3.5.2
ATROPOSELECTIVE
ARYLATION
BASED
ON
QUINONE
DERIVATIVES
68
3.5.3
ATROPOSELECTIVE
NUCLEOPHILIC
AROMATIC
SUBSTITUTION
71
3.6
CONCLUSION
72
REFERENCES
72
4
ENANTIOSELECTIVE
SYNTHESIS
OF
HETEROBIARYL
ATROPISOMERS
75
DAMIEN
BONNE
AND
JEAN
RODRIGUEZ
4.1
INTRODUCTION
75
4.2
ATROPISOMERIC
HETEROBIARYLS
FEATURING
TWO
SIX-MEMBERED
RINGS
75
4.2.1
FUNCTIONALIZATION
OF
HETEROBIARYLS
75
4.2.2
ATROPOSELECTIVE
RING
FORMATION
81
4.3
ATROPISOMERIC
HETEROBIARYLS
FEATURING
A
FIVE-MEMBERED
RING
87
4.3.1
FROM
PREFORMED
CYCLIC
SYSTEMS
87
4.3.2
FORMATION
OF
THE
HETEROBIARYL
AXIS
93
4.3.3
ATROPOSELECTIVE
RING
FORMATIONS
95
4.4
ATROPISOMERIC
HETEROBIARYLS
FEATURING
TWO
FIVE-MEMBERED
RINGS
103
4.4.1
FUNCTIONALIZATION
OF
HETEROBIARYLS
103
4.4.2
AROMATIZATION
OF
A
BIS-HETEROCYCLE
104
CONTENTS
VIL
4.4.3
ATROPOSELECTIVE
RING
FORMATIONS
105
4.5
CONCLUSION
AND
OUTLOOK
106
REFERENCES
106
5
ASYMMETRIC
SYNTHESIS
OF
NONBIARYL
ATROPISOMERS
109
MIRZA
A.
SAPUTRA,
MARIEL
CARDENAS,
AND
JEFFREY
L.
GUSTAFSON
5.1
INTRODUCTION
109
5.2
STYRENES
109
5.2.1
AXIALLY
CHIRAL
STYRENES
VIA
POINT-TO-AXIAL
CHIRALITY
TRANSFER
110
5.2.2
AXIALLY
CHIRAL
STYRENES
CONTROLLED
BY
CHIRAL
AUXILIARY
111
5.2.3
METAL-CATALYZED
ENANTIOSELECTIVE
SYNTHESIS
OF
AXIALLY
CHIRAL
STYRENE
111
5.2.4
ORGANOCATALYTIC
SYNTHESIS
OF
AXIALLY
CHIRAL
STYRENES
114
5.3
AMIDES
118
5.3.1
STEREOCHEMICAL
STABILITY
OF
ATROPISOMERIC
AMIDES
118
5.3.2
LITHIATION
OF
ATROPISOMERIC
AMIDES
TO
ACCESS
VARIOUS
ALKYLATIONS
118
5.3.3
SYNTHESES
OF
ATROPISOMERICALLY
STABLE
AMIDES
VIA
CHIRAL
AUXILIARIES
120
5.3.4
CATALYTIC
ASYMMETRIC
DIHYDROXYLATION
VIA
SHARPLESS
KR
CONDITIONS
121
5.3.5
ATROPOSELECTIVE
ALDOL
REACTIONS
VIA
DKR
APPROACH
121
5.3.6
ATROPOSELECTIVE
HALOGENATION
OF
AROMATIC
AMIDES
122
5.3.7
ATROPOSELECTIVE
[2
+
2
+
2]
CYCLOADDITION
TOWARD
ATROPISOMERICALLY
STABLE
BENZAMIDES
123
5.3.8
ENANTIOSELECTIVE
O-ALKYLATION
OF
AXIALLY
CHIRAL
AMIDES
123
5.4
DIARYL
ETHERS
124
5.4.1
RESOLUTION
STUDIES
OF
DIARYL
ETHERS
124
5.4.2
ENANTIOSELECTIVE
SYNTHESIS
OF
DIARYL
ETHER
125
5.4.3
ENZYME-CATALYZED
SYNTHESIS
OF
DIAIYL
ETHER
126
5.4.4
SYNTHESIS
OF
SCAFFOLDS
RELATED
TO
DIARYL
ETHERS
VIA
CSP
2
-H
ACTIVATION
127
5.5
ANILIDES
127
5.5.1
STEREOCHEMICAL
STABILITY
OF
AXIALLY
CHIRAL
ANILIDES
129
5.5.2
KINETIC
RESOLUTION
OR
DKR
TO
ACCESS
AXIALLY
CHIRAL
ANILIDES
129
5.5.3
SYNTHESIS
OF
AXIALLY
CHIRAL
ANILIDES
VIA
PLANAR
TO
AXIAL
CHIRALITY
TRANSFER
130
5.5.4
METAL-CATALYZED
SYNTHESIS
OF
CHIRAL
ANILIDES
131
5.5.5
ORGANOCATALYTIC
SYNTHESIS
OF
CHIRAL
ANILIDES
131
5.6
LACTAMS
AND
RELATED
SCAFFOLDS
133
5.6.1
STEREOCHEMICAL
STABILITY
OF
ATROPISOMERIC
LACTAMS
134
5.6.2
DIASTEREOSELECTIVE
CYCLIZATION
TOWARD
ATROPISOMERIC
LACTAMS
134
5.6.3
ENANTIOSELECTIVE
N-ARYLATION
TOWARD
LACTAM
ATROPISOMERS
134
5.6.4
ATROPOSELECTIVE
[2
+
2
+
2]
CYCLOADDITION
WITH
ISOCYANATES
135
5.6.5
CHIRAL
AUXILIARY
APPROACH
TOWARD
RESOLVING
ATROPISOMERIC
LACTAMS
136
5.6.6
ENANTIOSELECTIVE
BRONSTED
BASE-CATALYZED
TANDEM
ISOMERIZATION-MICHAEL
REACTIONS
TOWARD
ATROPISOMERIC
LACTAMS
136
5.7
DIARYL
AMINES
137
5.7.1
STEREOCHEMICAL
STABILITY
OF
DIARYL
AMINES
137
5.7.2
ATROPOSELECTIVE
APPROACHES
TOWARD DIARYL
AMINES
OR
RELATED
SCAFFOLDS
138
REFERENCES
138
VILI
CONTENTS
6
ASYMMETRIC
SYNTHESIS
OF
CHIRAL
ALLENES
141
JINBO
ZHAO
AND
YUNHE
XU
6.1
6.2
INTRODUCTION
141
SUBSTRATE
AND
REAGENT-CONTROLLED
CHIRAL
ALLENES
SYNTHESIS:
STOICHIOMETRIC
ASYMMETRIC
REACTIONS
142
6.2.1
6.2.1.1
CHIRALITY
TRANSFER
142
CHIRALITY
TRANSFER
FROM
PROPARGYL
ALCOHOL
AND
ITS
DERIVATIVES:
REARRANGEMENTS
142
6.2.1.2
PROCESSES
INVOLVING
STEREOSPECIFIC
REARRANGEMENTS
OF
PROPARGYL
AMINE
143
6.2.1.3
6.2.1.4
6.2.1.5
6.2.1.6
6.2.1.7
6.2.2
6.3
6.3.1
6.3.1.1
6.3.1.2
6.3.1.3
6.3.1.4
6.3.1.5
6.3.2
6.3.2.1
6.3.2.2
6.3.2.3
6.4
S
N
2
REACTION
145
PD-CATALYZED
STEREOSPECIFIC
REACTION
146
ISOMERIZATION
OF
PROPARGYL
METALS
148
CHIRALITY
TRANSFER
FROM
FUNCTIONALIZED
ALLYLIC
DERIVATIVES
149
CHIRALITY
TRANSFER
VIA
WITTIG
OLEFINATION
150
ASYMMETRIC
REACTION
WITH
STOICHIOMETRIC
CHIRAL
REAGENTS
151
CATALYTIC
ASYMMETRIC
STRATEGIES
FOR
THE
SYNTHESES
OF
CHIRAL
ALLENES
151
CATALYTIC
ENANTIOSELECTIVE
SYNTHESIS
FROM
ACHIRAL
SUBSTANCES
152
ENANTIOSELECTIVE
PROTON
MIGRATION
(ISOMERIZATION)
OF
ALKYNE
152
ENANTIOSELECTIVE
ADDITION
TO
1,3-ENYNE
154
ENANTIOSELECTIVE
ELIMINATION
REACTIONS
160
CATALYTIC
ASYMMETRIC
REACTIONS
INVOLVING
DIAZO
COMPOUNDS
161
DESYMMETRIZATION
162
ENANTIOSELECTIVE
ALLENE
SYNTHESIS
FROM
CHIRAL
SUBSTRATES
163
KINETIC
RESOLUTION
163
DYNAMIC
KINETIC
PROCESSES
164
DERACEMIZATION
167
CONCLUSION
AND
PERSPECTIVE
168
REFERENCES
169
7
ASYMMETRIC
SYNTHESIS
OF
AXIALLY
CHIRAL
NATURAL
PRODUCTS
173
HE
YANG
AND
WENJUN
TANG
7.1
7.2
7.2.1
7.2.1.1
7.2.1.2
7.2.2
7.2.2.1
7.2.2.2
7.3
7.3.1
7.3.2
7.4
7.4.1
INTRODUCTION
173
DIASTEREOSELECTIVE
COUPLING-POINT
TO
AXIAL
CHIRALITY
TRANSFER
175
INTRAMOLECULAR
DIASTEREOSELECTIVE
COUPLING
176
DIASTEREOSELECTIVE
COUPLING
ENABLED
BY
INTRINSIC
CHIRALITY
176
DIASTEREOSELECTIVE
COUPLING
FACILITATED
BY
CHIRAL
AUXILIARIES
182
INTERMOLECULAR
DIASTEREOSELECTIVE
ARYL
COUPLING
183
DIASTEREOSELECTIVE
COUPLING
ENABLED
BY
INTRINSIC
CHIRALITY
183
DIASTEREOSELECTIVE
COUPLING
FACILITATED
BY
CHIRAL
AUXILIARY
189
ATROPOSELECTIVE
ARYL
COUPLING
WITH
CHIRAL
CATALYST
191
CATALYTIC
OXIDATIVE
ARYL
COUPLING
191
TRANSITION
METAL-CATALYZED
ATROPOSELECTIVE
ARYL
COUPLING
194
ASYMMETRIC
TRANSFORMATION
OF
BIARYLS
196
DYNAMIC
KINETIC
RESOLUTION
OF
BIARYL
STRUCTURE
-
THE
LACTONE
METHOD
196
CONTENTS
IX
7.4.2
DESYMMETRIZATION
OF
PROSTEREOGENIC
BIARYLS
197
7.4.3
CATALYTIC
ATROPOSELECTIVE
C-H
FUNCTIONALIZATION
OF
BIARYLS
199
7.4.4
DIASTEREOSELECTIVE
SYNTHESIS
FROM
RACEMIC
BIARYLS
199
7.5
ATROPOSELECTIVE
AROMATIZATION
200
7.6
DIASTEREOSELECTIVE
MACROCYCLIZATION
202
7.7
CONCLUSIONS
AND
PERSPECTIVES
204
REFERENCES
204
PART
II
APPLICATIONS
209
8
ASYMMETRIC
TRANSFORMATIONS
211
GAOYUAN
MA
AND
MUKUND
P.
SIBI
8.1
ASYMMETRIC
TRANSFORMATION
OF
AXIALLY
CHIRAL
BIARYLS
AND
HETEROBIARYLS
211
8.1.1
ASYMMETRIC
TRANSFORMATIONS
WITH
PRESERVATION
OF
AXIALLY
CHIRAL
BACKBONE
212
8.1.2
ASYMMETRIC
TRANSFORMATIONS
WITH
AXIAL-TO-CENTRAL
CHIRALITY
TRANSFER
213
8.2
ASYMMETRIC
TRANSFORMATION
OF
AXIALLY
CHIRAL
NON-BIARYL
COMPOUNDS
214
8.2.1
CYCLOADDITIONS
AND
CYCLIZATIONS
214
8.2.1.1
[4
+
2]-CYCLOADDITION
214
8.2.1.2
[3
+
2]-CYCLOADDITION
214
8.2.1.3
RADICAL
CYCLIZATION
215
8.2.1.4
HECK
CYCLIZATION
217
8.2.1.5
CARBANIONIC
CYCLIZATION
217
8.2.2
REACTION
WITH
NUCLEOPHILES
218
8.2.3
REACTION
WITH
ELECTROPHILES
220
8.2.3.1
REACTIVITY
AS
ENOLATES
220
8.2.3.2
LITHIATION
221
8.2.3.3
REARRANGEMENTS
222
8.2.4
PHOTOREACTIONS
224
8.2.4.1
PHOTOCYCLOADDITION
224
8.2.4.2
PHOTOCYCLIZATION
225
8.2.4.3
HYDROGEN
ATOM
ABSTRACTION
226
8.3
ASYMMETRIC
TRANSFORMATION
OF
CHIRAL
ALLENES
226
8.3.1
CYCLIZATION
226
8.3.1.1
PALLADIUM-CATALYZED
CYCLIZATION
226
8.3.1.2
RHODIUM-CATALYZED
CYCLIZATION
228
8.3.1.3
GOLD-CATALYZED
CYCLIZATION
231
8.3.1.4
SILVER-CATALYZED
CYCLIZATION
231
8.3.1.5
ORGANIC
REAGENT-MEDIATED
CYCLIZATION
OF
CHIRAL
ALLENE
232
8.3.2
CYCLOADDITION
233
8.3.2.1
INTERMOLECULAR
CYCLOADDITION
233
X
CONTENTS
83.2.2
8.3.3
8.3.3.1
8.33.2
8.3.4
8.4
INTRAMOLECULAR
CYCLOADDITION
234
REACTION
WITH
NUCLEOPHILES
236
REACTION
WITH
CARBON
NUCLEOPHILES
236
REACTION
WITH
HETEROATOM
NUCLEOPHILES
238
CHIRAL
ALLENE
AS
NUCLEOPHILES
240
CONCLUSION
242
REFERENCES
243
9
APPLICATION
FOR
AXIALLY
CHIRAL
LIGANDS
245
BING-CHAO
DA
AND
BIN
TAN
9.1
9.2
9.2.1
9.2.2
9.2.3
9.2.4
9.3
9.3.1
9.3.2
9.3.3
9.4
9.4.1
9.4.2
9.4.3
9.4.4
9.4.5
9.5
9.5.1
9.6
9.6.1
9.6.2
9.6.3
9.6.4
9.7
9.8
INTRODUCTION
245
MONODENTATE
PHOSPHINES
246
ASYMMETRIC
HYDROGENATIONS
246
ASYMMETRIC
HYDROSILYLATION
OF
OLEFINS
248
ASYMMETRIC
ALLYLIC
SUBSTITUTIONS
249
MISCELLANEOUS
CATALYTIC
ASYMMETRIC
TRANSFORMATIONS
250
DIPHOSPHINE
LIGANDS
252
HYDROGENATION
REACTIONS
252
C
-
C
BOND
FORMATION
255
C
-
X
BOND
FORMATION
257
PHOSPHORAMIDITE
AND
PHOSPHAMIDE
LIGANDS
259
ASYMMETRIC
CONJUGATE
ADDITION
WITH
ORGANOMETALLIC
NUCLEOPHILES
259
HYDROGENATION
260
HYDROBORATION/HYDROSILYLATION
REACTIONS
261
ALLYLIC
SUBSTITUTIONS
262
OTHER
ASYMMETRIC
TRANSFORMATIONS
263
N-P
LIGANDS
264
APPLICATIONS
OF
N,
P-LIGANDS
265
C
2
-SYMMETRIC
DIOLS
267
MUKAIYAMA
ALDOL
CONDENSATION
REACTIONS
267
DIELS-ALDER
REACTION
268
ARRANGEMENT
REACTION
269
REDUCTIVE
REACTIONS
269
OTHER
AXIALLY
CHIRAL
LIGANDS
IN
ASYMMETRIC
TRANSFORMATIONS
270
CONCLUSIONS
271
REFERENCES
271
10
APPLICATION
FOR
AXIALLY
CHIRAL
ORGANOCATALYSTS
275
TAKAHIKO
AKIYAMA
10.1
10.2
10.2.1
10.2.2
10.3
INTRODUCTION
275
CHIRAL
BRONSTED
ACID
CATALYSTS
276
CHIRAL
BINOL
DERIVATIVES
276
CHIRAL
PHOSPHORIC
ACID
276
CHIRAL
COUNTERANION
CATALYSTS
AND
CHIRAL
PHASE
TRANSFER
CATALYSTS
285
CONTENTS
INDEX
317
10.4
10.5
BRONSTED
BASE
CATALYST
288
LEWIS
BASE
CATALYSTS
289
REFERENCES
294
11
APPLICATION
IN
DRUGS
AND
MATERIALS
297
YONG-BIN
WANG,
SHAO-HUA
XIANG,
AND
BIN
TAN
11.1
DRUGS
297
11.2
CHIRAL
RECOGNITION
302
11.3
CHIRAL
ADDITIVES
IN
LIQUID
CRYSTALS
307
REFERENCES
313
XI
|
| adam_txt |
V
CONTENTS
PREFACE
XIII
PART
I
ASYMMETRIC
SYNTHESIS
1
1
INTRODUCTION
AND
CHARACTERISTICS
3
YONG-BIN
WANG,
SHAO-HUA
XIANG,
AND
BIN
TAN
1.1
INTRODUCTION
AND
CLASSIFICATION
3
1.2
SPECIFICATION
OF
CONFIGURATION
9
REFERENCES
11
2
METAL-CATALYZED
ASYMMETRIC
SYNTHESIS
OF
BIARYL
ATROPISOMERS
13
TAO
ZHOU
AND
BING-FENG
SHI
2.1
INTRODUCTION
13
2.2
BIARYL
COUPLING
13
2.2.1
CROSS-COUPLING
13
2.2.1.1
KUMADA-TAMAO-CORRIU
CROSS-COUPLING
14
2.2.1.2
NEGISHI
CROSS-COUPLING
15
2.2.1.3
SUZUKI-MIYAURA
CROSS-COUPLING
15
2.2.2
OTHER
TYPES
OF
CROSS-COUPLING
24
2.2.3
OXIDATIVE
COUPLING
24
2.2.3.1
CU-CATALYZED
OXIDATIVE
COUPLING
25
2.2.3.2
OXIDATIVE
COUPLING
REACTIONS
WITH
OTHER
METALS
27
2.3
DESYMMETRIZATION
AND
(DYNAMIC)
KINETIC
RESOLUTION
VIA
FUNCTIONAL
GROUP
TRANSFORMATION
29
2.3.1
DESYMMETRIZATION
OF
PROCHIRAL
BIARYLS
29
2.3.2
KINETIC
RESOLUTION
OF
RACEMIC
AXIALLY
CHIRAL
BIARYLS
30
2.3.3
DYNAMIC
KINETIC
RESOLUTION
OF
RACEMIC
AXIALLY
CHIRAL
BIARYLS
30
2.3.4
RING-OPENING
REACTIONS
32
2.4
FORMATION
OF
AROMATIC
RING
VIA
[2
+
2
+
2]
CYCLOADDITION
35
2.4.1
COBALT-CATALYZED
ENANTIOSELECTIVE
[2
+
2
+
2]
CYCLOADDITIONS
35
2.4.2
RHODIUM-CATALYZED
ENANTIOSELECTIVE
[2
+
2
+
2]
CYCLOADDITIONS
36
VI
CONTENTS
2.4.3
IRIDIUM-CATALYZED
ENANTIOSELECTIVE
[2
+
2
+
2]
CYCLOADDITIONS
36
2.5
C
-
H
BOND
FUNCTIONALIZATION
38
2.5.1
CHIRAL
CATALYST-CONTROLLED
C
-
H
BOND
FUNCTIONALIZATION
38
2.5.2
CHIRAL
AUXILIARY-INDUCED
C
-
H
BOND
FUNCTIONALIZATION
40
2.5.3
ATROPOSELECTIVE
C
-
H
ARYLATION
40
2.6
SUMMARY
AND
CONCLUSIONS
42
REFERENCES
42
3
ORGANOCATALYTIC
ASYMMETRIC
SYNTHESIS
OF
BIARYL
ATROPISOMERS
47
SHAOYU
LI,
SHAO-HUA
XIANG,
AND
BIN
TAN
3.1
INTRODUCTION
47
3.2
ATROPOSELECTIVE
SYNTHESIS
OF
BIARYLS
BY
KINETIC
RESOLUTION
STRATEGY
47
3.2.1
CONVENTIONAL
KINETIC
RESOLUTION
47
3.2.1.1
KINETIC
RESOLUTION
VIA
ASYMMETRIC
ALKYLATION
48
3.2.1.2
KINETIC
RESOLUTION
VIA
ASYMMETRIC
ACYLATION
50
3.2.1.3
KINETIC
RESOLUTION
VIA
ASYMMETRIC
TRANSFER
HYDROGENATION
AND
MICHAEL
ADDITION
53
3.2.2
DYNAMIC
KINETIC
RESOLUTION
STRATEGY
54
3.2.2.1
DKR
VIA
ASYMMETRIC
ELECTROPHILIC
BROMINATION
54
3.2.2.2
DKR
VIA
ASYMMETRIC
NUCLEOPHILIC
ADDITION
56
3.2.2.3
DKR
BASED
ON
ASYMMETRIC
RING-OPENING/EXPANSION
TRANSFORMATION
57
3.3
ATROPOSELECTIVE
SYNTHESIS
OF
BIARYLS
BY
DESYMMETRIZATION
STRATEGY
59
3.4
ATROPOSELECTIVE
ARENE
FORMATION
TO
ACCESS
AXIALLY
CHIRAL
BIARYLS
61
3.4.1
INTRAMOLECULAR
ATROPOSELECTIVE
ARENE
FORMATION
61
3.4.2
ATROPOSELECTIVE
ARENE
FORMATION
VIA
INTERMOLECULAR
ANNULATION
63
3.5
ATROPOSELECTIVE
SYNTHESIS
OF
BIARYLS
VIA
DIRECT
C-H
ARYLATION
STRATEGY
67
3.5.1
ORGANOCATALYTIC
C-H
ARYLATION
BY
[3,3]-SIGMATROPIC
REARRANGEMENT
67
3.5.2
ATROPOSELECTIVE
ARYLATION
BASED
ON
QUINONE
DERIVATIVES
68
3.5.3
ATROPOSELECTIVE
NUCLEOPHILIC
AROMATIC
SUBSTITUTION
71
3.6
CONCLUSION
72
REFERENCES
72
4
ENANTIOSELECTIVE
SYNTHESIS
OF
HETEROBIARYL
ATROPISOMERS
75
DAMIEN
BONNE
AND
JEAN
RODRIGUEZ
4.1
INTRODUCTION
75
4.2
ATROPISOMERIC
HETEROBIARYLS
FEATURING
TWO
SIX-MEMBERED
RINGS
75
4.2.1
FUNCTIONALIZATION
OF
HETEROBIARYLS
75
4.2.2
ATROPOSELECTIVE
RING
FORMATION
81
4.3
ATROPISOMERIC
HETEROBIARYLS
FEATURING
A
FIVE-MEMBERED
RING
87
4.3.1
FROM
PREFORMED
CYCLIC
SYSTEMS
87
4.3.2
FORMATION
OF
THE
HETEROBIARYL
AXIS
93
4.3.3
ATROPOSELECTIVE
RING
FORMATIONS
95
4.4
ATROPISOMERIC
HETEROBIARYLS
FEATURING
TWO
FIVE-MEMBERED
RINGS
103
4.4.1
FUNCTIONALIZATION
OF
HETEROBIARYLS
103
4.4.2
AROMATIZATION
OF
A
BIS-HETEROCYCLE
104
CONTENTS
VIL
4.4.3
ATROPOSELECTIVE
RING
FORMATIONS
105
4.5
CONCLUSION
AND
OUTLOOK
106
REFERENCES
106
5
ASYMMETRIC
SYNTHESIS
OF
NONBIARYL
ATROPISOMERS
109
MIRZA
A.
SAPUTRA,
MARIEL
CARDENAS,
AND
JEFFREY
L.
GUSTAFSON
5.1
INTRODUCTION
109
5.2
STYRENES
109
5.2.1
AXIALLY
CHIRAL
STYRENES
VIA
POINT-TO-AXIAL
CHIRALITY
TRANSFER
110
5.2.2
AXIALLY
CHIRAL
STYRENES
CONTROLLED
BY
CHIRAL
AUXILIARY
111
5.2.3
METAL-CATALYZED
ENANTIOSELECTIVE
SYNTHESIS
OF
AXIALLY
CHIRAL
STYRENE
111
5.2.4
ORGANOCATALYTIC
SYNTHESIS
OF
AXIALLY
CHIRAL
STYRENES
114
5.3
AMIDES
118
5.3.1
STEREOCHEMICAL
STABILITY
OF
ATROPISOMERIC
AMIDES
118
5.3.2
LITHIATION
OF
ATROPISOMERIC
AMIDES
TO
ACCESS
VARIOUS
ALKYLATIONS
118
5.3.3
SYNTHESES
OF
ATROPISOMERICALLY
STABLE
AMIDES
VIA
CHIRAL
AUXILIARIES
120
5.3.4
CATALYTIC
ASYMMETRIC
DIHYDROXYLATION
VIA
SHARPLESS
KR
CONDITIONS
121
5.3.5
ATROPOSELECTIVE
ALDOL
REACTIONS
VIA
DKR
APPROACH
121
5.3.6
ATROPOSELECTIVE
HALOGENATION
OF
AROMATIC
AMIDES
122
5.3.7
ATROPOSELECTIVE
[2
+
2
+
2]
CYCLOADDITION
TOWARD
ATROPISOMERICALLY
STABLE
BENZAMIDES
123
5.3.8
ENANTIOSELECTIVE
O-ALKYLATION
OF
AXIALLY
CHIRAL
AMIDES
123
5.4
DIARYL
ETHERS
124
5.4.1
RESOLUTION
STUDIES
OF
DIARYL
ETHERS
124
5.4.2
ENANTIOSELECTIVE
SYNTHESIS
OF
DIARYL
ETHER
125
5.4.3
ENZYME-CATALYZED
SYNTHESIS
OF
DIAIYL
ETHER
126
5.4.4
SYNTHESIS
OF
SCAFFOLDS
RELATED
TO
DIARYL
ETHERS
VIA
CSP
2
-H
ACTIVATION
127
5.5
ANILIDES
127
5.5.1
STEREOCHEMICAL
STABILITY
OF
AXIALLY
CHIRAL
ANILIDES
129
5.5.2
KINETIC
RESOLUTION
OR
DKR
TO
ACCESS
AXIALLY
CHIRAL
ANILIDES
129
5.5.3
SYNTHESIS
OF
AXIALLY
CHIRAL
ANILIDES
VIA
PLANAR
TO
AXIAL
CHIRALITY
TRANSFER
130
5.5.4
METAL-CATALYZED
SYNTHESIS
OF
CHIRAL
ANILIDES
131
5.5.5
ORGANOCATALYTIC
SYNTHESIS
OF
CHIRAL
ANILIDES
131
5.6
LACTAMS
AND
RELATED
SCAFFOLDS
133
5.6.1
STEREOCHEMICAL
STABILITY
OF
ATROPISOMERIC
LACTAMS
134
5.6.2
DIASTEREOSELECTIVE
CYCLIZATION
TOWARD
ATROPISOMERIC
LACTAMS
134
5.6.3
ENANTIOSELECTIVE
N-ARYLATION
TOWARD
LACTAM
ATROPISOMERS
134
5.6.4
ATROPOSELECTIVE
[2
+
2
+
2]
CYCLOADDITION
WITH
ISOCYANATES
135
5.6.5
CHIRAL
AUXILIARY
APPROACH
TOWARD
RESOLVING
ATROPISOMERIC
LACTAMS
136
5.6.6
ENANTIOSELECTIVE
BRONSTED
BASE-CATALYZED
TANDEM
ISOMERIZATION-MICHAEL
REACTIONS
TOWARD
ATROPISOMERIC
LACTAMS
136
5.7
DIARYL
AMINES
137
5.7.1
STEREOCHEMICAL
STABILITY
OF
DIARYL
AMINES
137
5.7.2
ATROPOSELECTIVE
APPROACHES
TOWARD DIARYL
AMINES
OR
RELATED
SCAFFOLDS
138
REFERENCES
138
VILI
CONTENTS
6
ASYMMETRIC
SYNTHESIS
OF
CHIRAL
ALLENES
141
JINBO
ZHAO
AND
YUNHE
XU
6.1
6.2
INTRODUCTION
141
SUBSTRATE
AND
REAGENT-CONTROLLED
CHIRAL
ALLENES
SYNTHESIS:
STOICHIOMETRIC
ASYMMETRIC
REACTIONS
142
6.2.1
6.2.1.1
CHIRALITY
TRANSFER
142
CHIRALITY
TRANSFER
FROM
PROPARGYL
ALCOHOL
AND
ITS
DERIVATIVES:
REARRANGEMENTS
142
6.2.1.2
PROCESSES
INVOLVING
STEREOSPECIFIC
REARRANGEMENTS
OF
PROPARGYL
AMINE
143
6.2.1.3
6.2.1.4
6.2.1.5
6.2.1.6
6.2.1.7
6.2.2
6.3
6.3.1
6.3.1.1
6.3.1.2
6.3.1.3
6.3.1.4
6.3.1.5
6.3.2
6.3.2.1
6.3.2.2
6.3.2.3
6.4
S
N
2'
REACTION
145
PD-CATALYZED
STEREOSPECIFIC
REACTION
146
ISOMERIZATION
OF
PROPARGYL
METALS
148
CHIRALITY
TRANSFER
FROM
FUNCTIONALIZED
ALLYLIC
DERIVATIVES
149
CHIRALITY
TRANSFER
VIA
WITTIG
OLEFINATION
150
ASYMMETRIC
REACTION
WITH
STOICHIOMETRIC
CHIRAL
REAGENTS
151
CATALYTIC
ASYMMETRIC
STRATEGIES
FOR
THE
SYNTHESES
OF
CHIRAL
ALLENES
151
CATALYTIC
ENANTIOSELECTIVE
SYNTHESIS
FROM
ACHIRAL
SUBSTANCES
152
ENANTIOSELECTIVE
PROTON
MIGRATION
(ISOMERIZATION)
OF
ALKYNE
152
ENANTIOSELECTIVE
ADDITION
TO
1,3-ENYNE
154
ENANTIOSELECTIVE
ELIMINATION
REACTIONS
160
CATALYTIC
ASYMMETRIC
REACTIONS
INVOLVING
DIAZO
COMPOUNDS
161
DESYMMETRIZATION
162
ENANTIOSELECTIVE
ALLENE
SYNTHESIS
FROM
CHIRAL
SUBSTRATES
163
KINETIC
RESOLUTION
163
DYNAMIC
KINETIC
PROCESSES
164
DERACEMIZATION
167
CONCLUSION
AND
PERSPECTIVE
168
REFERENCES
169
7
ASYMMETRIC
SYNTHESIS
OF
AXIALLY
CHIRAL
NATURAL
PRODUCTS
173
HE
YANG
AND
WENJUN
TANG
7.1
7.2
7.2.1
7.2.1.1
7.2.1.2
7.2.2
7.2.2.1
7.2.2.2
7.3
7.3.1
7.3.2
7.4
7.4.1
INTRODUCTION
173
DIASTEREOSELECTIVE
COUPLING-POINT
TO
AXIAL
CHIRALITY
TRANSFER
175
INTRAMOLECULAR
DIASTEREOSELECTIVE
COUPLING
176
DIASTEREOSELECTIVE
COUPLING
ENABLED
BY
INTRINSIC
CHIRALITY
176
DIASTEREOSELECTIVE
COUPLING
FACILITATED
BY
CHIRAL
AUXILIARIES
182
INTERMOLECULAR
DIASTEREOSELECTIVE
ARYL
COUPLING
183
DIASTEREOSELECTIVE
COUPLING
ENABLED
BY
INTRINSIC
CHIRALITY
183
DIASTEREOSELECTIVE
COUPLING
FACILITATED
BY
CHIRAL
AUXILIARY
189
ATROPOSELECTIVE
ARYL
COUPLING
WITH
CHIRAL
CATALYST
191
CATALYTIC
OXIDATIVE
ARYL
COUPLING
191
TRANSITION
METAL-CATALYZED
ATROPOSELECTIVE
ARYL
COUPLING
194
ASYMMETRIC
TRANSFORMATION
OF
BIARYLS
196
DYNAMIC
KINETIC
RESOLUTION
OF
BIARYL
STRUCTURE
-
THE
LACTONE
METHOD
196
CONTENTS
IX
7.4.2
DESYMMETRIZATION
OF
PROSTEREOGENIC
BIARYLS
197
7.4.3
CATALYTIC
ATROPOSELECTIVE
C-H
FUNCTIONALIZATION
OF
BIARYLS
199
7.4.4
DIASTEREOSELECTIVE
SYNTHESIS
FROM
RACEMIC
BIARYLS
199
7.5
ATROPOSELECTIVE
AROMATIZATION
200
7.6
DIASTEREOSELECTIVE
MACROCYCLIZATION
202
7.7
CONCLUSIONS
AND
PERSPECTIVES
204
REFERENCES
204
PART
II
APPLICATIONS
209
8
ASYMMETRIC
TRANSFORMATIONS
211
GAOYUAN
MA
AND
MUKUND
P.
SIBI
8.1
ASYMMETRIC
TRANSFORMATION
OF
AXIALLY
CHIRAL
BIARYLS
AND
HETEROBIARYLS
211
8.1.1
ASYMMETRIC
TRANSFORMATIONS
WITH
PRESERVATION
OF
AXIALLY
CHIRAL
BACKBONE
212
8.1.2
ASYMMETRIC
TRANSFORMATIONS
WITH
AXIAL-TO-CENTRAL
CHIRALITY
TRANSFER
213
8.2
ASYMMETRIC
TRANSFORMATION
OF
AXIALLY
CHIRAL
NON-BIARYL
COMPOUNDS
214
8.2.1
CYCLOADDITIONS
AND
CYCLIZATIONS
214
8.2.1.1
[4
+
2]-CYCLOADDITION
214
8.2.1.2
[3
+
2]-CYCLOADDITION
214
8.2.1.3
RADICAL
CYCLIZATION
215
8.2.1.4
HECK
CYCLIZATION
217
8.2.1.5
CARBANIONIC
CYCLIZATION
217
8.2.2
REACTION
WITH
NUCLEOPHILES
218
8.2.3
REACTION
WITH
ELECTROPHILES
220
8.2.3.1
REACTIVITY
AS
ENOLATES
220
8.2.3.2
LITHIATION
221
8.2.3.3
REARRANGEMENTS
222
8.2.4
PHOTOREACTIONS
224
8.2.4.1
PHOTOCYCLOADDITION
224
8.2.4.2
PHOTOCYCLIZATION
225
8.2.4.3
HYDROGEN
ATOM
ABSTRACTION
226
8.3
ASYMMETRIC
TRANSFORMATION
OF
CHIRAL
ALLENES
226
8.3.1
CYCLIZATION
226
8.3.1.1
PALLADIUM-CATALYZED
CYCLIZATION
226
8.3.1.2
RHODIUM-CATALYZED
CYCLIZATION
228
8.3.1.3
GOLD-CATALYZED
CYCLIZATION
231
8.3.1.4
SILVER-CATALYZED
CYCLIZATION
231
8.3.1.5
ORGANIC
REAGENT-MEDIATED
CYCLIZATION
OF
CHIRAL
ALLENE
232
8.3.2
CYCLOADDITION
233
8.3.2.1
INTERMOLECULAR
CYCLOADDITION
233
X
CONTENTS
83.2.2
8.3.3
8.3.3.1
8.33.2
8.3.4
8.4
INTRAMOLECULAR
CYCLOADDITION
234
REACTION
WITH
NUCLEOPHILES
236
REACTION
WITH
CARBON
NUCLEOPHILES
236
REACTION
WITH
HETEROATOM
NUCLEOPHILES
238
CHIRAL
ALLENE
AS
NUCLEOPHILES
240
CONCLUSION
242
REFERENCES
243
9
APPLICATION
FOR
AXIALLY
CHIRAL
LIGANDS
245
BING-CHAO
DA
AND
BIN
TAN
9.1
9.2
9.2.1
9.2.2
9.2.3
9.2.4
9.3
9.3.1
9.3.2
9.3.3
9.4
9.4.1
9.4.2
9.4.3
9.4.4
9.4.5
9.5
9.5.1
9.6
9.6.1
9.6.2
9.6.3
9.6.4
9.7
9.8
INTRODUCTION
245
MONODENTATE
PHOSPHINES
246
ASYMMETRIC
HYDROGENATIONS
246
ASYMMETRIC
HYDROSILYLATION
OF
OLEFINS
248
ASYMMETRIC
ALLYLIC
SUBSTITUTIONS
249
MISCELLANEOUS
CATALYTIC
ASYMMETRIC
TRANSFORMATIONS
250
DIPHOSPHINE
LIGANDS
252
HYDROGENATION
REACTIONS
252
C
-
C
BOND
FORMATION
255
C
-
X
BOND
FORMATION
257
PHOSPHORAMIDITE
AND
PHOSPHAMIDE
LIGANDS
259
ASYMMETRIC
CONJUGATE
ADDITION
WITH
ORGANOMETALLIC
NUCLEOPHILES
259
HYDROGENATION
260
HYDROBORATION/HYDROSILYLATION
REACTIONS
261
ALLYLIC
SUBSTITUTIONS
262
OTHER
ASYMMETRIC
TRANSFORMATIONS
263
N-P
LIGANDS
264
APPLICATIONS
OF
N,
P-LIGANDS
265
C
2
-SYMMETRIC
DIOLS
267
MUKAIYAMA
ALDOL
CONDENSATION
REACTIONS
267
DIELS-ALDER
REACTION
268
ARRANGEMENT
REACTION
269
REDUCTIVE
REACTIONS
269
OTHER
AXIALLY
CHIRAL
LIGANDS
IN
ASYMMETRIC
TRANSFORMATIONS
270
CONCLUSIONS
271
REFERENCES
271
10
APPLICATION
FOR
AXIALLY
CHIRAL
ORGANOCATALYSTS
275
TAKAHIKO
AKIYAMA
10.1
10.2
10.2.1
10.2.2
10.3
INTRODUCTION
275
CHIRAL
BRONSTED
ACID
CATALYSTS
276
CHIRAL
BINOL
DERIVATIVES
276
CHIRAL
PHOSPHORIC
ACID
276
CHIRAL
COUNTERANION
CATALYSTS
AND
CHIRAL
PHASE
TRANSFER
CATALYSTS
285
CONTENTS
INDEX
317
10.4
10.5
BRONSTED
BASE
CATALYST
288
LEWIS
BASE
CATALYSTS
289
REFERENCES
294
11
APPLICATION
IN
DRUGS
AND
MATERIALS
297
YONG-BIN
WANG,
SHAO-HUA
XIANG,
AND
BIN
TAN
11.1
DRUGS
297
11.2
CHIRAL
RECOGNITION
302
11.3
CHIRAL
ADDITIVES
IN
LIQUID
CRYSTALS
307
REFERENCES
313
XI |
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| discipline_str_mv | Chemie / Pharmazie |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV047481648 |
| illustrated | Illustrated |
| index_date | 2024-07-03T18:12:46Z |
| indexdate | 2024-07-10T09:13:19Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527347124 3527347127 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-032883134 |
| oclc_num | 1284997448 |
| open_access_boolean | |
| owner | DE-19 DE-BY-UBM DE-11 |
| owner_facet | DE-19 DE-BY-UBM DE-11 |
| physical | xiv, 322 Seiten Illustrationen 24.4 cm x 17 cm |
| publishDate | 2021 |
| publishDateSearch | 2021 |
| publishDateSort | 2021 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Axially chiral compounds asymmetric synthesis and applications edited by Tan Bin Weinheim WILEY-VCH [2021] © 2021 xiv, 322 Seiten Illustrationen 24.4 cm x 17 cm txt rdacontent n rdamedia nc rdacarrier Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Axiale Chiralität (DE-588)4766198-7 gnd rswk-swf Chirale Verbindungen (DE-588)4348527-3 gnd rswk-swf Chemie Chemistry Homogene Katalyse Homogeneous Catalysis Methods - Synthesis & Techniques Organische Chemie / Methoden, Synthesen, Verfahren Physical Chemistry Physikalische Chemie CH42: Homogene Katalyse CH81: Organische Chemie / Methoden, Synthesen, Verfahren CH90: Physikalische Chemie (DE-588)4143413-4 Aufsatzsammlung gnd-content Chirale Verbindungen (DE-588)4348527-3 s Axiale Chiralität (DE-588)4766198-7 s Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Tan, Bin (DE-588)1244775401 edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, EPUB 978-3-527-82518-9 Erscheint auch als Online-Ausgabe, PDF 978-3-527-82516-5 Erscheint auch als Online-Ausgabe, OBOOK 978-3-527-82517-2 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032883134&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Axially chiral compounds asymmetric synthesis and applications Asymmetrische Synthese (DE-588)4135603-2 gnd Axiale Chiralität (DE-588)4766198-7 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| subject_GND | (DE-588)4135603-2 (DE-588)4766198-7 (DE-588)4348527-3 (DE-588)4143413-4 |
| title | Axially chiral compounds asymmetric synthesis and applications |
| title_auth | Axially chiral compounds asymmetric synthesis and applications |
| title_exact_search | Axially chiral compounds asymmetric synthesis and applications |
| title_exact_search_txtP | Axially chiral compounds asymmetric synthesis and applications |
| title_full | Axially chiral compounds asymmetric synthesis and applications edited by Tan Bin |
| title_fullStr | Axially chiral compounds asymmetric synthesis and applications edited by Tan Bin |
| title_full_unstemmed | Axially chiral compounds asymmetric synthesis and applications edited by Tan Bin |
| title_short | Axially chiral compounds |
| title_sort | axially chiral compounds asymmetric synthesis and applications |
| title_sub | asymmetric synthesis and applications |
| topic | Asymmetrische Synthese (DE-588)4135603-2 gnd Axiale Chiralität (DE-588)4766198-7 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| topic_facet | Asymmetrische Synthese Axiale Chiralität Chirale Verbindungen Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032883134&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT tanbin axiallychiralcompoundsasymmetricsynthesisandapplications AT wileyvch axiallychiralcompoundsasymmetricsynthesisandapplications |