Chiral building blocks in asymmetric synthesis: synthesis and applications
Gespeichert in:
| Weitere Verfasser: | , |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
[2022]
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | xx, 668 Seiten Illustrationen, Diagramme |
| ISBN: | 9783527349463 |
Internformat
MARC
| LEADER | 00000nam a22000008c 4500 | ||
|---|---|---|---|
| 001 | BV048489176 | ||
| 003 | DE-604 | ||
| 005 | 20230322 | ||
| 007 | t | ||
| 008 | 220927s2022 gw a||| |||| 00||| eng d | ||
| 015 | |a 22,N12 |2 dnb | ||
| 016 | 7 | |a 1253682518 |2 DE-101 | |
| 020 | |a 9783527349463 |c hbk. |9 978-3-527-34946-3 | ||
| 035 | |a (OCoLC)1349539825 | ||
| 035 | |a (DE-599)DNB1253682518 | ||
| 040 | |a DE-604 |b ger |e rda | ||
| 041 | 0 | |a eng | |
| 044 | |a gw |c XA-DE-BW | ||
| 049 | |a DE-29T |a DE-83 |a DE-703 |a DE-11 |a DE-19 | ||
| 084 | |a VK 5800 |0 (DE-625)147412:253 |2 rvk | ||
| 084 | |a VK 5500 |0 (DE-625)147401:253 |2 rvk | ||
| 084 | |8 1\p |a 540 |2 23sdnb | ||
| 245 | 1 | 0 | |a Chiral building blocks in asymmetric synthesis |b synthesis and applications |c edited by Elżbieta Wojaczyńska, Jacek Wojaczyński |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2022] | |
| 264 | 4 | |c © 2022 | |
| 300 | |a xx, 668 Seiten |b Illustrationen, Diagramme | ||
| 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 Chirale Verbindungen |0 (DE-588)4348527-3 |2 gnd |9 rswk-swf |
| 653 | |a Asymmetrische Synthese | ||
| 653 | |a CH30: Technische u. Industrielle Chemie | ||
| 653 | |a CH40: Katalyse | ||
| 653 | |a CH81: Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 653 | |a Catalysis | ||
| 653 | |a Chemie | ||
| 653 | |a Chemische Synthese | ||
| 653 | |a Chemistry | ||
| 653 | |a Industrial Chemistry | ||
| 653 | |a Katalyse | ||
| 653 | |a Methods - Synthesis & Techniques | ||
| 653 | |a Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 653 | |a Technische u. Industrielle Chemie | ||
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |D s |
| 689 | 0 | 1 | |a Chirale Verbindungen |0 (DE-588)4348527-3 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Wojaczyńska, Elżbieta |0 (DE-588)1271039168 |4 edt | |
| 700 | 1 | |a Wojaczyński, Jacek |4 edt | |
| 710 | 2 | |a Wiley-VCH |0 (DE-588)16179388-5 |4 pbl | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-83418-1 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-83419-8 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, oBook |z 978-3-527-83420-4 |
| 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=033866684&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-033866684 | ||
| 883 | 1 | |8 1\p |a vlb |d 20220318 |q DE-101 |u https://d-nb.info/provenance/plan#vlb | |
Datensatz im Suchindex
| _version_ | 1804184448506265600 |
|---|---|
| adam_text | V
CONTENTS
PREFACE
XV
FOREWORD
XIX
1
ENANTIOSELECTIVE
SYNTHESIS
OF
CYCLOPROPENES
1
VIRGINIE
CARRERAS
AND
THIERRY
OLLEVIER
1.1
1.1.1
1.1.2
1.2
1.2.1
1.2.2
1.2.3
1.2.4
1.2.5
1.2.6
1.3
INTRODUCTION
1
SYNTHESIS
OF
CYCLOPROPENES
1
REACTIVITY
OF
CYCLOPROPENES
2
METAL-CATALYZED
ENANTIOSELECTIVE
SYNTHESES
OF
CYCLOPROPENES
3
RHODIUM
CATALYSIS
3
COPPER
CATALYSIS
9
IRIDIUM
CATALYSIS
9
COBALT-CHIRAL
PORPHYRIN
CATALYSIS
10
GOLD
AND
SILVER
CATALYSIS
10
BIOCATALYSIS
13
OTHER
SYNTHETIC
ROUTES
AND
DERIVATIZATIONS
OF
ENANTIOENRICHED
CYCLOPROPENES
13
1.4
SUMMARY
AND
PROSPECT
15
REFERENCES
15
2
CHIRAL
HETEROCYCLES
FOR
ASYMMETRIC
SYNTHESIS
21
RADOVAN
SEBESTA
AND
TIBOR
PEHASKA
2.1
2.2
2.3
2.4
2.5
INTRODUCTION
21
SMALL-RING
HETEROCYCLES
21
MEDIUM-RING
ALIPHATIC
HETEROCYCLES
29
OTHER
HETEROCYCLIC
BUILDING
BLOCKS
37
CONCLUSIONS
38
REFERENCES
39
3
SATURATED
HETEROCYCLES
AS
CHIRAL
AUXILIARIES
43
AGNIESZKA
PAZDZIERNIOK-HOLEWA
AND
SEBASTIAN
STECKO
3.1
3.2
INTRODUCTION
43
PROLINE-DERIVED
CHIRAL
AUXILIARIES
43
VI
CONTENTS
3.3
3.4
3.5
3.6
3.7
3.8
2,5-TRANS-DISUBSTITUTED
PYRROLIDINES
46
HETEROCYCLIC
HYDRAZONES
50
OXAZOLIDINE-BASED
CHIRAL
AUXILIARIES
57
CAMPHOR-BASED
CHIRAL
HETEROCYCLIC
AUXILIARIES
60
PHOSPHONAMIDE-BASED
CHIRAL
AUXILIARIES
68
SCHOLLKOPF
S
CHIRAL
AUXILIARIES
AND
RELATED
HETEROCYCLES
FOR
THE
ASYMMETRIC
SYNTHESIS
OF
A-AMINO
ACIDS
72
3.9
CONCLUSIONS
73
REFERENCES
74
4
TRANS-1,2-DIAMINOCYCLOHEXANE
AND
ITS
DERIVATIVES
IN
ASYMMETRIC
ORGANOCATALYSIS
87
MICHAL
KOPYT,
MICHAL
P.
GLOWACKI,
AND
PIOTR
KWIATKOWSKI
4.1
4.2
4.3
INTRODUCTION
87
TRANS-1,2-DIAMINOCYCLOHEXANE-BASED
ORGANOCATALYSTS
89
APPLICATION
OF
TRANS
1,2-DIAMINOCYCLOHEXANE
DERIVATIVES
IN
ASYMMETRIC
ORGANOCATALYSIS
96
4.3.1
4.3.2
4.3.3
MICHAEL
ADDITIONS
OF
MALONATE
ESTERS
TO
NITROSTYRENE
97
MICHAEL
ADDITIONS
OF
OTHER
1,3-DICARBONYLS
TO
NITROSTYRENE
98
MICHAEL
ADDITIONS
OF
ENOLIZABLE
KETONES
AND
ALDEHYDES
TO
NITROSTYRENE
99
4.3.4
4.3.5
4.3.6
4.3.7
4.3.8
4.3.9
4.3.10
4.3.11
4.3.12
4.3.13
4.3.14
4.3.15
4.4
MICHAEL
ADDITIONS
OF
OTHER
CARBON
NUCLEOPHILES
TO
NITROSTYRENE
101
MICHAEL
ADDITIONS
OF
HETERONUCLEOPHILES
TO
NITROSTYRENE
102
MICHAEL
REACTIONS
OF
ENONES
102
MICHAEL
REACTIONS
OF
BENZYLIDENE
PYRUVATES
103
REACTIONS
OF
ISATIN-DERIVED
MICHAEL
ACCEPTORS
104
MICHAEL
REACTIONS
OF
MALEIMIDES
105
ALDOL
REACTION
AND
OTHER
ASYMMETRIC
REACTIONS
OF
ALDEHYDES
106
REACTIONS
OF
ISATINS
107
REACTIONS
OF
IMINES
108
PICTET-SPENGLER-TYPE
REACTIONS
109
REACTIONS
OF
NITROGEN
ELECTROPHILES
110
MISCELLANEOUS
REACTIONS
111
CONCLUSIONS
113
REFERENCES
113
5
DIKETOPIPERAZINES
AS
CHIRAL
BUILDING
BLOCKS
139
JUAN
DOMINGO
SANCHEZ,
JUAN
FRANCISCO
GONZALEZ,
AND
JOSE
CARLOS
MENENDEZ
5.1
5.2
5.2.1
5.2.1.1
5.2.1.2
5.2.1.3
5.2.1.4
INTRODUCTION
139
A
BRIEF
OVERVIEW
OF
THE
SYNTHESIS
OF
2,5-DIKETOPIPERAZINES
140
METHODS
THAT
CREATE
THE
N1
-
C
2
BOND
140
CYCLIZATION
OF
DIPEPTIDES
140
CYCLIZATION
OF
UGI
REACTION
PRODUCTS
141
STAUDINGER/INTRAMOLECULAR
AZA-WITTIG
SEQUENCES
142
DKP
FORMATION
COUPLED
TO
ADDITIONAL
CYCLIZATION
REACTIONS
143
CONTENTS
VII
5.2.2
5.2.2.1
5.2.2.2
5.2.3
5.2.3.1
5.23.2
5.2.4
5.3
5.3.1
5.3.2
5.3.3
5.3.4
5.4
5.4.1
5.4.2
5.4.2.1
5.4.2.2
5.4.23
5.4.2.4
5.4.2.5
5.4.2.6
5.4.3
METHODS
THAT
CREATE
THE
N1
-
C
6
BOND
143
FROM
A-HALOACYL
AMINO
ACIDS
143
BY
AZA-MICHAEL
ADDITIONS
144
METHODS
THAT
CREATE
TWO
BONDS
144
FORMATION
OF
N1
-
C
6
AND
N4
-
C3
BONDS
144
FORMATION
OF
N1
-
C
2
AND
N1
-
C
6
BONDS
144
BIOTECHNOLOGICAL
METHODS
145
2,5-DIKETOPIPERAZINES
IN
DRUG
SYNTHESIS
145
SYNTHESIS
OF
TADALAFIL
145
SYNTHESIS
OF
TROFINETIDE
(NNZ-2591)
146
SYNTHESIS
OF
APLAVIROC
147
SYNTHESIS
OF
RETOSIBAN
147
NATURAL
PRODUCT
SYNTHESIS
148
ASYMMETRIC
SYNTHESIS
OF
AMINO
ACIDS
148
SYNTHESIS
OF
ALKALOIDS
CONTAINING
A
2,5-DIKETOPIPERAZINE
CORE
149
TRYPROSTATIN
B
149
SPIROTRYPROSTATIN
B
150
STEPHACIDINB
150
VERSICOLAMIDE
B
151
VARIECOLORTIDE
A
151
DIDEOXYVERTICILLIN
152
SYNTHESIS
OF
ALKALOIDS
CONTAINING
A
MODIFIED
2,5-DIKETOPIPERAZINE
CORE
153
5.43.1
5.43.2
5.4.33
5.43.4
5.5
ARDEEMIN
153
PHAKELLIN
153
SARCODONINS
154
ECTEINASCIDIN
743
155
CONCLUSIONS
156
REFERENCES
157
6
AMINO
ACIDS
AS
CHIRAL
BUILDING
BLOCKS
161
ELISABETE
P.
CARREIRO
AND
ANTHONY
J.
BURKE
6.1
6.2
6.2.1
6.3
6.3.1
63.1.1
63.1.2
6.3.2
INTRODUCTION
161
CHIRAL
SUBSTRATES/REAGENTS
161
CHIRAL
AMINO
ACIDS
161
CHIRAL
AUXILIARIES
165
CHIRAL
PYRROLIDINE
AUXILIARIES
166
YAMADA
AUXILIARY
166
ENDERS
AUXILIARIES
166
SCHOLLKOPF
S
BIS-LACTIM
ETHERS
(SCHOLLKOPF
CHIRAL
AUXILIARIES):
GLYCINE
ENOLATE
EQUIVALENTS
167
6.3.3
6.33.1
6.33.2
6.4
OXAZOLIDINONES
168
EVANS
CHIRAL
AUXILIARY
168
SUPERQUAT
CHIRAL
AUXILIARIES
170
OXAZABOROLIDINES
172
VIII
CONTENTS
6.5
6.5.1
6.5.2
6.5.2.1
6.5.2.2
6.5.23
6.5.2.4
6.5.3
6.5.4
6.6
ORGANOCATALYSTS
172
AMINO
ACID
AND
PEPTIDE-BASED
ORGANOCATALYSTS
173
ORGANOCATALYSTS
BASED
ON
PROLINE
174
PROLINE
174
PROLINE
AMIDES
AND
PEPTIDES
177
DIARYLPROLINOL
SILYL
ETHER
AND
ANALOGOUS
SYSTEMS
179
OTHER
PROLINE
ANALOGUES
184
IMIDAZOLIDINONES
187
AMIDINE-BASED
ORGANOCATALYSTS
190
CONCLUSIONS
191
REFERENCES
191
7
CARBOHYDRATE-BASED
CATALYSTS
AND
AUXILIARIES
IN
ORGANIC
SYNTHESIS
197
SEBASTIAN
BAS
F
SZYMON
BUDA,
AND
JACEK
MFYNARSKI
7.1
7.1.1
7.1.2
7.1.3
7.1.4
7.2
7.2.1
7.2.2
CHIRAL
AUXILIARIES
197
CHIRAL
IMINES
198
CHIRAL
OXAZOLIDINONES
202
CHIRAL
ESTERS
204
CHIRAL
ETHERS
211
CHIRAL
CATALYSTS
213
CHIRAL
COMPLEXES
214
ORGANOCATALYSTS
220
REFERENCES
225
8
MONOTERPENES
AS
CHIRAL
BUILDING
BLOCKS
235
AGATA
J.
PACUTA-MISZEWSKA,
MAGDALENA
OBIEZIURSKA-FABISIAK,
AND
JACEK
SCIANOWSKI
8.1
8.2
8.3
8.4
8.5
INTRODUCTION
235
ACYCLIC
MONOTERPENE
BUILDING
BLOCKS
237
MONOCYCLIC
TERPENE
BUILDING
BLOCKS
243
BICYCLIC
TERPENE
BUILDING
BLOCKS
256
CONCLUSIONS
261
REFERENCES
262
9
DITERPENE
ACIDS
AS
STARTING
MATERIALS
FOR
THE
SYNTHESIS
OF
BIOLOGICALLY
ACTIVE
COMPOUNDS
267
IGNACIO
E.
TOBAL,
ALEJANDRO
M.
RONCERO,
ROSALINA
F.
MORO,
DOVID
DIEZ,
AND
ISIDRO
S.
MARCOS
9.1
9.1.1
9.1.2
9.1.3
9.1.3.1
ZAMORANIC
ACID
1
AS
A PRECURSOR
OF
INTERESTING
COMPOUNDS
269
SYNTHESIS
OF
CHRYSOLIC
ACID
AND
ISOFREGENEDOL
269
SYNTHESIS
OF
NEW
LABDANE
DITERPENOIDS
271
SYNTHESIS
OF
DRIMANES
272
SYNTHESIS
OF
POLIGODIAL,
WARBURGANAL,
PERENIPORIN
A,
AND
PERENIPORIN
B
273
CONTENTS
IX
9.1.3.2
9.1.4
9.1.4.1
9.1.4.2
9.1.5
9.2
SYNTHESIS
OF
ISODRIMENINOL
273
SYNTHESIS
OF
LABDANOLIDES
AND
FUROLABDANES
274
SYNTHESIS
OF
(+)-LIMONIDILACTONE
274
SYNTHESIS
OF
GUTIERREZIANOLIC
ACID
274
SYNTHESIS
OF
TRI
AND
TETRACYCLIC
DITERPENES
275
ENT-HALIMIC
ACID
AS
A
PRECURSOR
OF
BIOLOGICALLY
ACTIVE
COMPOUNDS
AND
OTHER
INTERESTING
DERIVATIVES
276
9.2.1
9.2.1.1
9.2.1.2
9.2.1.3
9.2.2
9.2.3
9.2.3.1
9.2.4
9.2.5
9.2.5.1
9.2.5.2
9.2.5.3
9.2.6
9.2.7
9.2.7.1
9.2.7.2
9.2.7.3
9.2.7.4
SYNTHESIS
OF
ENT-HALIMANOLIDES
278
SYNTHESIS
OF
NATURAL
ENT-HALIMANOLIDE
SYNTHESIS
278
SYNTHESIS
OF
A
AND
P-HYDROXYHALIMANOLIDES
280
SYNTHESIS
OF
FURO-ENT-HALIMANOLIDE
280
SYNTHESIS
OF
CHETTAPHANINS
281
SYNTHESIS
OF
SESTERTERPENOLIDES
281
SYNTHESIS
OF
SESTERTERPENOLIDES,
ANALOGUES
OF
DYSIDIOLIDE
282
SYNTHESIS
OF
SESTERTERPENOLIDE
AND
GLYCEROL
HYBRIDS
283
SYNTHESIS
OF
REARRANGED
COMPOUNDS
283
SYNTHESIS
OF
ENT-LABDANES
FROM
ENT-HALIMANES
283
SYNTHESIS
OF
ABEOPICRASANES
FROM
ENT-HALIMANES
284
SYNTHESIS
OF
[4.3.3]PROPELLANES
FROM
ENT-HALIMANES
285
SYNTHESIS
OF
QUINONE/HYDROQUINONE
SESQUITERPENES
285
SYNTHESIS
OF
SESQUI
AND
DITERPENE
ALKALOIDS
286
SYNTHESIS
OF
THE
DITERPENE
ALKALOID,
(+)-AGELASINE
C
287
SYNTHESIS
OF
DITERPENE
ALKALOID,
(+)-THIERSINDOLE
C
288
SYNTHESIS
OF
SESQUITERPENYL
INDOLES
289
SYNTHESIS
OF
SESQUITERPENE
INDOLES,
ANALOGUES
OF
POLYALTHENOL
AND
PENTACYCLINDOLE
289
ACKNOWLEDGMENTS
290
REFERENCES
291
10
ALKALOIDS
AS
CHIRAL
BUILDING
BLOCKS,
AUXILIARIES,
LIGANDS,
AND
MOLECULAR
DIVERSITY
297
KAROL
KACPRZAK,
ELZBIETA
WOJACZYNSKA,
ANDRZEJ
TROCHIMCZUK,
FRANZ
STEPPELER,
AND
JACEK
WOJACZYNSKI
10.1
10.2
10.3
10.4
10.5
10.6
10.7
INTRODUCTION
297
EPHEDRA
ALKALOIDS
303
TOBACCO
ALKALOIDS
(NICOTINE
AND
ANABASINE)
311
LUPIN
ALKALOIDS
314
CINCHONA
ALKALOIDS
325
TROPANE
ALKALOIDS
335
ALKALOIDS
AS
BUILDING
BLOCKS
IN
THE
SYNTHESES
OF
CHIRAL
POLYMERS
AND
THEIR
APPLICATION
338
ACKNOWLEDGMENTS
345
REFERENCES
345
CONTENTS
11
CHIRAL
BUILDING
BLOCKS
FOR
TOTAL
STEROID
SYNTHESIS
AND
THE
USE
OF
STEROIDS
AS
CHIRAL
BUILDING
BLOCKS
IN
ORGANIC
SYNTHESIS
367
IZABELLA
JASTRZ^BSKA
AND
DOUGLAS
F.
COVEY
11.1
11.2
11.2.1
11.2.2
11.2.3
11.2.4
11.2.5
11.2.6
11.2.7
11.2.8
11.2.9
11.3
11.3.1
11.3.2
11.3.3
INTRODUCTION
367
CHIRAL
BUILDING
BLOCKS
FOR
THE
CONSTRUCTION
OF
STEROIDS
368
CHIRAL
BUILDING
BLOCK
1
(CBB
1)
368
CHIRAL
BUILDING
BLOCK
2
(CBB
2)
369
CHIRAL
BUILDING
BLOCK
3
(CBB
3)
370
CHIRAL
BUILDING
BLOCK
4
(CBB
4)
370
CHIRAL
BUILDING
BLOCK
5
(CBB
5)
371
CHIRAL
BUILDING
BLOCK
6
(CBB
6)
372
CHIRAL
BUILDING
BLOCK
7
(CBB
7)
373
CHIRAL
BUILDING
BLOCK
8
(CBB
8)
374
CHIRAL
BUILDING
BLOCK
9
(CBB
9)
375
STEROIDS
AS
CHIRAL
BUILDING
BLOCKS
376
SYNTHESIS
OF
C-NOR-D-HOMO-STEROIDS
376
PREGNENOLONE
AS
A
CHIRAL
BUILDING
BLOCK:
SYNTHESIS
OF
CYCLOCITRINOL
377
4
ANDROSTENE-3,17-DIONE
AS
A
CHIRAL
BUILDING
BLOCK:
SYNTHESIS
OF
VULGAROBUFOTOXIN
377
11.3.4
11.3.4.1
11.3.4.2
11.3.4.3
11.3.4.4
11.3.5
11.3.5.1
11.3.5.2
ERGOSTEROL
AS
A
CHIRAL
BUILDING
BLOCK
378
SYNTHESIS
OF
PLEUROCIN
A/MATSUTAKONE
378
SYNTHESIS
OF
STROPHASTEROL
A
379
SYNTHESIS
OF
HERBARULIDE
379
SYNTHESIS
OF
PINNIGORGIOL
E
AND
PINNIGORGIOL
B
380
TIGOGENIN
AS
A
CHIRAL
BUILDING
BLOCK
381
SYNTHESIS
OF
CLATHSTEROL
381
SYNTHESIS
OF
NORTRITERPENOID
PROPINDILACTONE
G
383
REFERENCES
384
12
CHIRAL
ORGANOPHOSPHORUS
COMPOUNDS
IN
ASYMMETRIC
SYNTHESIS
389
ELZBIETA
LASTAWIECKA,
SYLWIA
SOWA,
KATARZYNA
SZWACZKO,
KAMIL
DZIUBA,
MAREK
STANKEVII,
AND
ADAM
WTODARCZYK
12.1
12.2
INTRODUCTION
389
ORGANOPHOSPHORUS
COMPOUNDS
WITH
INCORPORATED
CHIRAL
TERPENE
MOIETIES
389
12.3
12.4
12.5
ORGANOPHOSPHORUS
COMPOUNDS
WITH
AXIAL
CHIRALITY
397
CHIRAL
AMINOPHOSPHONIC
ACIDS
AND
THEIR
ANALOGS
406
STEREOGENIC
ORGANOPHOSPHORUS
COMPOUNDS
WITH
P
-
N
AND/OR
P
-
0
BONDS
418
12.6
SUMMARY
425
REFERENCES
426
CONTENTS
XI
13
ORGANOSULFUR
COMPOUNDS
AS
CHIRAL
BUILDING
BLOCKS
441
MARIA
A.M.
CAPOZZI
AND
COSIMO
CARDELLICCHIO
13.1
13.2
13.3
13.3.1
13.3.2
13.3.3
13.3.4
13.3.5
13.4
13.4.1
13.4.2
13.5
STATE
OF
THE
ART
441
INTRODUCTION
441
THE
TRADITION
442
MENTHYL
(RS)
OR
(SS)-P-TOLUENESULFINATE
(ANDERSEN
S
REAGENT)
442
(R)-P-TOLUENESULFINAMIDE
(DAVIS
REAGENT)
449
(IS,
2R,
5S)-MENTHYL
(S)-P-BROMOPHENYLSULFINATE
451
(R)-TERT-BUTHYL
TERT-BUTANETHIOSULFINATE
(ELLMAN
S
REAGENT)
452
SULFOXIMINES
454
IDEAS
FOR
THE
FUTURE
454
DAG-CHEMISTRY
454
ARYL
BENZYL
SULFOXIDES
455
CONCLUSIONS
456
REFERENCES
456
14
ORGANOSELENIUM
COMPOUNDS
AS
CHIRAL
BUILDING
BLOCKS
463
LUANA
BAGNOLI
AND
CLAUDIO
SANTI
14.1
14.2
INTRODUCTION
463
ASYMMETRIC
SELENOFUCTIONALIZATION
REACTIONS
PROMOTED
BY
ELECTROPHILIC
SELENIUM
REAGENTS
463
14.3
VINYL
SELENONES
AS
IMPORTANT
BUILDING
BLOCKS
IN
ASYMMETRIC
PROCESSES
470
14.4
ASYMMETRIC
SYNTHESIS
BY
MICHAEL-INITIATED
RING
CLOSURE
REACTIONS
FROM
VINYL
SELENONES
470
14.5
FUNCTIONALIZATION
OF
VINYL
SELENONES
OF
CARBOHYDRATES
AND
NUCLEOTIDES
472
14.6
ASYMMETRIC
ORGANOCATALYTIC
TRANSFORMATIONS
STARTING
WITH
VINYL
SELENONES
475
14.7
CONCLUSION
481
REFERENCES
481
15
ALLENES
AS
CHIRAL
BUILDING
BLOCKS
IN
ASYMMETRIC
SYNTHESIS
489
RAFAT
LOSKA
AND
ALICJA
WASILEWSKA-ROSA
15.1
15.2
15.3
INTRODUCTION
489
NUCLEOPHILIC
ADDITION
AND
SUBSTITUTION
490
ALLENYLZINC
AND
INDIUM
REAGENTS,
ALLENYLSILANES
AND
ALLENYLSTANNANES
491
15.4
15.5
15.6
15.7
EPOXIDATION,
AZIRIDINATION,
AND
SILACYCLOPROPANATION
OF
ALLENES
494
NAZAROV
CYCLIZATION
OF
ALLENYL
VINYL
KETONES
499
NUCLEOPHILIC
CYCLIZATION
AND
ADDITION
PROMOTED
BY
ELECTROPHILES
500
CYCLOISOMERIZATION
AND
OTHER
REACTIONS
CATALYZED
BY
TRANSITION
METALS
510
XII
CONTENTS
15.8
CYCLOADDITION
OF
ALLENES
513
ACKNOWLEDGMENTS
51
7
REFERENCES
517
16
THE
SYNTHESIS
AND
APPLICATION
OF
BINOL
DERIVATIVES
AS
EFFECTIVE
BUILDING
BLOCKS
FOR
CATALYSTS
EMPLOYED
IN
ENANTIOSELECTIVE
SYNTHESIS
523
JANUSZ
JURCZAK,
PATRYK
NIEDBALA,
AND
AGATA
TYSZKA-GUMKOWSKA
16.1
16.2
16.2.1
16.2.2
16.2.3
16.3
16.4
16.4.1
16.4.2
16.4.3
16.4.4
16.4.5
16.4.6
INTRODUCTION
523
BINOL
DERIVATIVES
WITH
FREE
HYDROXYL
GROUPS
524
ALLYLBORATION
REACTIONS
525
CONJUGATED
ADDITION
REACTIONS
526
OTHER
EXAMPLES
526
ONIUM
SALTS AS
CHARGED
CATALYSTS
IN
PTC
529
CHIRAL
PHOSPHORIC
ACIDS
DERIVED
FROM
BINOL
PLATFORM
533
MICHAEL
REACTION
533
FRIEDEL-CRAFTS
REACTION
534
DIELS-ALDER
REACTION
535
1
,3-DIPOLAR
CYCLOADDITION
538
MULTICOMPONENT
REACTIONS
539
OTHER
EXAMPLES
543
ACKNOWLEDGMENTS
544
REFERENCES
545
17
CHIRAL
ACENES:
SYNTHESIS
AND
APPLICATIONS
551
ANDREA
NITTI,
GIOVANNI
PREDA
T
AND
DARIO
PASINI
17.1
17.2
17.2.1
17.2.1.1
17.2.1.2
17.2.1.3
17.2.2
17.2.2.1
17.2.2.2
17.2.2.3
17.2.2.4
17.2.2.5
17.2.3
17.2.4
17.2.4.1
17.2.4.2
17.2.4.3
17.3
17.4
INTRODUCTION
551
CHIRAL
CARBO[N]HELICENES
552
STRUCTURE
AND
PROPERTIES
OF
HELICENES
553
TOPOLOGICAL
DESCRIPTION
553
AROMATICITY
AND
OPTOELECTRONIC
PROPERTIES
554
CHIRALITY
OF
HELICENE
557
RACEMIC
SYNTHESIS
AND
OPTICAL
RESOLUTION
METHODS
559
METAL-FREE
PHOTOCYCLIZATION
REACTIONS
559
DIELS-ALDER
CYCLOADDITION
560
FRIEDEL-CRAFTS-TYPE
CYCLIZATION
560
METAL-CATALYZED
REACTIONS
561
OPTICAL
RESOLUTION
564
ASYMMETRIC
SYNTHESES
565
APPLICATION OF
CHIRAL
CARBO[N]HELICENES
567
HELICENES
IN
CATALYSIS
567
HELICENES
IN
ORGANIC
ELECTRONICS
569
HELICENES
IN
BIOCHEMISTRY
571
TWISTACENES
571
CHIRAL
NANOBELTS
572
INDEX
653
CONTENTS
|
XIII
17.5
CONCLUDING
REMARKS
575
REFERENCES
575
18
2-AZA-21-CARBAPORPHYRIN
IN
CONSTRUCTION
OF
CHIRAL
SUPRAMOLECULAR
ASSEMBLIES
583
SEBASTIAN
KONIARZ
AND
PIOTR
J.
CHMIELEWSKI
18.1
18.2
18.2.1
18.2.2
18.3
18.3.1
18.3.2
18.4
PREFACE
583
MONOMERS
586
FREE
BASES
586
METAL
COMPLEXES
596
DIMERS
AND
OLIGOMERS
601
COORDINATING
OLIGOMERS
602
COVALENTLY
LINKED
DIMERS
606
SUMMARY
AND
OUTLOOK
611
REFERENCES
612
19
CATENANE,
ROTAXANE,
AND
MOLECULAR
KNOT
CHIRAL
BUILDING
BLOCKS
623
JEAN-CLAUDE
CHAMBRON
19.1
19.2
19.3
19.4
19.5
19.6
19.6.1
19.6.2
19.6.3
19.6.3.1
19.6.3.2
19.7
INTRODUCTION
623
ELEMENTS
OF
MOLECULAR
TOPOLOGY
624
TOPOLOGICAL
CHIRALITY
AND
CHIRAL
CATENANES
627
CHIRAL
[2]ROTAXANES
631
TOPOLOGICALLY
CHIRAL
MOLECULAR
KNOTS
634
CATENANES,
ROTAXANES,
AND
KNOTS
AS
CHIRAL
BUILDING
BLOCKS
638
CATENANES
639
ROTAXANES
639
MOLECULAR
KNOTS
642
COVALENT
LINKING
OF
TREFOIL
KNOT
BUILDING
BLOCKS
642
COMPOSITE
KNOTS
644
CONCLUSIONS
648
REFERENCES
650
|
| adam_txt |
V
CONTENTS
PREFACE
XV
FOREWORD
XIX
1
ENANTIOSELECTIVE
SYNTHESIS
OF
CYCLOPROPENES
1
VIRGINIE
CARRERAS
AND
THIERRY
OLLEVIER
1.1
1.1.1
1.1.2
1.2
1.2.1
1.2.2
1.2.3
1.2.4
1.2.5
1.2.6
1.3
INTRODUCTION
1
SYNTHESIS
OF
CYCLOPROPENES
1
REACTIVITY
OF
CYCLOPROPENES
2
METAL-CATALYZED
ENANTIOSELECTIVE
SYNTHESES
OF
CYCLOPROPENES
3
RHODIUM
CATALYSIS
3
COPPER
CATALYSIS
9
IRIDIUM
CATALYSIS
9
COBALT-CHIRAL
PORPHYRIN
CATALYSIS
10
GOLD
AND
SILVER
CATALYSIS
10
BIOCATALYSIS
13
OTHER
SYNTHETIC
ROUTES
AND
DERIVATIZATIONS
OF
ENANTIOENRICHED
CYCLOPROPENES
13
1.4
SUMMARY
AND
PROSPECT
15
REFERENCES
15
2
CHIRAL
HETEROCYCLES
FOR
ASYMMETRIC
SYNTHESIS
21
RADOVAN
SEBESTA
AND
TIBOR
PEHASKA
2.1
2.2
2.3
2.4
2.5
INTRODUCTION
21
SMALL-RING
HETEROCYCLES
21
MEDIUM-RING
ALIPHATIC
HETEROCYCLES
29
OTHER
HETEROCYCLIC
BUILDING
BLOCKS
37
CONCLUSIONS
38
REFERENCES
39
3
SATURATED
HETEROCYCLES
AS
CHIRAL
AUXILIARIES
43
AGNIESZKA
PAZDZIERNIOK-HOLEWA
AND
SEBASTIAN
STECKO
3.1
3.2
INTRODUCTION
43
PROLINE-DERIVED
CHIRAL
AUXILIARIES
43
VI
CONTENTS
3.3
3.4
3.5
3.6
3.7
3.8
2,5-TRANS-DISUBSTITUTED
PYRROLIDINES
46
HETEROCYCLIC
HYDRAZONES
50
OXAZOLIDINE-BASED
CHIRAL
AUXILIARIES
57
CAMPHOR-BASED
CHIRAL
HETEROCYCLIC
AUXILIARIES
60
PHOSPHONAMIDE-BASED
CHIRAL
AUXILIARIES
68
SCHOLLKOPF
S
CHIRAL
AUXILIARIES
AND
RELATED
HETEROCYCLES
FOR
THE
ASYMMETRIC
SYNTHESIS
OF
A-AMINO
ACIDS
72
3.9
CONCLUSIONS
73
REFERENCES
74
4
TRANS-1,2-DIAMINOCYCLOHEXANE
AND
ITS
DERIVATIVES
IN
ASYMMETRIC
ORGANOCATALYSIS
87
MICHAL
KOPYT,
MICHAL
P.
GLOWACKI,
AND
PIOTR
KWIATKOWSKI
4.1
4.2
4.3
INTRODUCTION
87
TRANS-1,2-DIAMINOCYCLOHEXANE-BASED
ORGANOCATALYSTS
89
APPLICATION
OF
TRANS
1,2-DIAMINOCYCLOHEXANE
DERIVATIVES
IN
ASYMMETRIC
ORGANOCATALYSIS
96
4.3.1
4.3.2
4.3.3
MICHAEL
ADDITIONS
OF
MALONATE
ESTERS
TO
NITROSTYRENE
97
MICHAEL
ADDITIONS
OF
OTHER
1,3-DICARBONYLS
TO
NITROSTYRENE
98
MICHAEL
ADDITIONS
OF
ENOLIZABLE
KETONES
AND
ALDEHYDES
TO
NITROSTYRENE
99
4.3.4
4.3.5
4.3.6
4.3.7
4.3.8
4.3.9
4.3.10
4.3.11
4.3.12
4.3.13
4.3.14
4.3.15
4.4
MICHAEL
ADDITIONS
OF
OTHER
CARBON
NUCLEOPHILES
TO
NITROSTYRENE
101
MICHAEL
ADDITIONS
OF
HETERONUCLEOPHILES
TO
NITROSTYRENE
102
MICHAEL
REACTIONS
OF
ENONES
102
MICHAEL
REACTIONS
OF
BENZYLIDENE
PYRUVATES
103
REACTIONS
OF
ISATIN-DERIVED
MICHAEL
ACCEPTORS
104
MICHAEL
REACTIONS
OF
MALEIMIDES
105
ALDOL
REACTION
AND
OTHER
ASYMMETRIC
REACTIONS
OF
ALDEHYDES
106
REACTIONS
OF
ISATINS
107
REACTIONS
OF
IMINES
108
PICTET-SPENGLER-TYPE
REACTIONS
109
REACTIONS
OF
NITROGEN
ELECTROPHILES
110
MISCELLANEOUS
REACTIONS
111
CONCLUSIONS
113
REFERENCES
113
5
DIKETOPIPERAZINES
AS
CHIRAL
BUILDING
BLOCKS
139
JUAN
DOMINGO
SANCHEZ,
JUAN
FRANCISCO
GONZALEZ,
AND
JOSE
CARLOS
MENENDEZ
5.1
5.2
5.2.1
5.2.1.1
5.2.1.2
5.2.1.3
5.2.1.4
INTRODUCTION
139
A
BRIEF
OVERVIEW
OF
THE
SYNTHESIS
OF
2,5-DIKETOPIPERAZINES
140
METHODS
THAT
CREATE
THE
N1
-
C
2
BOND
140
CYCLIZATION
OF
DIPEPTIDES
140
CYCLIZATION
OF
UGI
REACTION
PRODUCTS
141
STAUDINGER/INTRAMOLECULAR
AZA-WITTIG
SEQUENCES
142
DKP
FORMATION
COUPLED
TO
ADDITIONAL
CYCLIZATION
REACTIONS
143
CONTENTS
VII
5.2.2
5.2.2.1
5.2.2.2
5.2.3
5.2.3.1
5.23.2
5.2.4
5.3
5.3.1
5.3.2
5.3.3
5.3.4
5.4
5.4.1
5.4.2
5.4.2.1
5.4.2.2
5.4.23
5.4.2.4
5.4.2.5
5.4.2.6
5.4.3
METHODS
THAT
CREATE
THE
N1
-
C
6
BOND
143
FROM
A-HALOACYL
AMINO
ACIDS
143
BY
AZA-MICHAEL
ADDITIONS
144
METHODS
THAT
CREATE
TWO
BONDS
144
FORMATION
OF
N1
-
C
6
AND
N4
-
C3
BONDS
144
FORMATION
OF
N1
-
C
2
AND
N1
-
C
6
BONDS
144
BIOTECHNOLOGICAL
METHODS
145
2,5-DIKETOPIPERAZINES
IN
DRUG
SYNTHESIS
145
SYNTHESIS
OF
TADALAFIL
145
SYNTHESIS
OF
TROFINETIDE
(NNZ-2591)
146
SYNTHESIS
OF
APLAVIROC
147
SYNTHESIS
OF
RETOSIBAN
147
NATURAL
PRODUCT
SYNTHESIS
148
ASYMMETRIC
SYNTHESIS
OF
AMINO
ACIDS
148
SYNTHESIS
OF
ALKALOIDS
CONTAINING
A
2,5-DIKETOPIPERAZINE
CORE
149
TRYPROSTATIN
B
149
SPIROTRYPROSTATIN
B
150
STEPHACIDINB
150
VERSICOLAMIDE
B
151
VARIECOLORTIDE
A
151
DIDEOXYVERTICILLIN
152
SYNTHESIS
OF
ALKALOIDS
CONTAINING
A
MODIFIED
2,5-DIKETOPIPERAZINE
CORE
153
5.43.1
5.43.2
5.4.33
5.43.4
5.5
ARDEEMIN
153
PHAKELLIN
153
SARCODONINS
154
ECTEINASCIDIN
743
155
CONCLUSIONS
156
REFERENCES
157
6
AMINO
ACIDS
AS
CHIRAL
BUILDING
BLOCKS
161
ELISABETE
P.
CARREIRO
AND
ANTHONY
J.
BURKE
6.1
6.2
6.2.1
6.3
6.3.1
63.1.1
63.1.2
6.3.2
INTRODUCTION
161
CHIRAL
SUBSTRATES/REAGENTS
161
CHIRAL
AMINO
ACIDS
161
CHIRAL
AUXILIARIES
165
CHIRAL
PYRROLIDINE
AUXILIARIES
166
YAMADA
AUXILIARY
166
ENDERS
AUXILIARIES
166
SCHOLLKOPF
S
BIS-LACTIM
ETHERS
(SCHOLLKOPF
CHIRAL
AUXILIARIES):
GLYCINE
ENOLATE
EQUIVALENTS
167
6.3.3
6.33.1
6.33.2
6.4
OXAZOLIDINONES
168
EVANS
'
CHIRAL
AUXILIARY
168
SUPERQUAT
CHIRAL
AUXILIARIES
170
OXAZABOROLIDINES
172
VIII
CONTENTS
6.5
6.5.1
6.5.2
6.5.2.1
6.5.2.2
6.5.23
6.5.2.4
6.5.3
6.5.4
6.6
ORGANOCATALYSTS
172
AMINO
ACID
AND
PEPTIDE-BASED
ORGANOCATALYSTS
173
ORGANOCATALYSTS
BASED
ON
PROLINE
174
PROLINE
174
PROLINE
AMIDES
AND
PEPTIDES
177
DIARYLPROLINOL
SILYL
ETHER
AND
ANALOGOUS
SYSTEMS
179
OTHER
PROLINE
ANALOGUES
184
IMIDAZOLIDINONES
187
AMIDINE-BASED
ORGANOCATALYSTS
190
CONCLUSIONS
191
REFERENCES
191
7
CARBOHYDRATE-BASED
CATALYSTS
AND
AUXILIARIES
IN
ORGANIC
SYNTHESIS
197
SEBASTIAN
BAS
F
SZYMON
BUDA,
AND
JACEK
MFYNARSKI
7.1
7.1.1
7.1.2
7.1.3
7.1.4
7.2
7.2.1
7.2.2
CHIRAL
AUXILIARIES
197
CHIRAL
IMINES
198
CHIRAL
OXAZOLIDINONES
202
CHIRAL
ESTERS
204
CHIRAL
ETHERS
211
CHIRAL
CATALYSTS
213
CHIRAL
COMPLEXES
214
ORGANOCATALYSTS
220
REFERENCES
225
8
MONOTERPENES
AS
CHIRAL
BUILDING
BLOCKS
235
AGATA
J.
PACUTA-MISZEWSKA,
MAGDALENA
OBIEZIURSKA-FABISIAK,
AND
JACEK
SCIANOWSKI
8.1
8.2
8.3
8.4
8.5
INTRODUCTION
235
ACYCLIC
MONOTERPENE
BUILDING
BLOCKS
237
MONOCYCLIC
TERPENE
BUILDING
BLOCKS
243
BICYCLIC
TERPENE
BUILDING
BLOCKS
256
CONCLUSIONS
261
REFERENCES
262
9
DITERPENE
ACIDS
AS
STARTING
MATERIALS
FOR
THE
SYNTHESIS
OF
BIOLOGICALLY
ACTIVE
COMPOUNDS
267
IGNACIO
E.
TOBAL,
ALEJANDRO
M.
RONCERO,
ROSALINA
F.
MORO,
DOVID
DIEZ,
AND
ISIDRO
S.
MARCOS
9.1
9.1.1
9.1.2
9.1.3
9.1.3.1
ZAMORANIC
ACID
1
AS
A PRECURSOR
OF
INTERESTING
COMPOUNDS
269
SYNTHESIS
OF
CHRYSOLIC
ACID
AND
ISOFREGENEDOL
269
SYNTHESIS
OF
NEW
LABDANE
DITERPENOIDS
271
SYNTHESIS
OF
DRIMANES
272
SYNTHESIS
OF
POLIGODIAL,
WARBURGANAL,
PERENIPORIN
A,
AND
PERENIPORIN
B
273
CONTENTS
IX
9.1.3.2
9.1.4
9.1.4.1
9.1.4.2
9.1.5
9.2
SYNTHESIS
OF
ISODRIMENINOL
273
SYNTHESIS
OF
LABDANOLIDES
AND
FUROLABDANES
274
SYNTHESIS
OF
(+)-LIMONIDILACTONE
274
SYNTHESIS
OF
GUTIERREZIANOLIC
ACID
274
SYNTHESIS
OF
TRI
AND
TETRACYCLIC
DITERPENES
275
ENT-HALIMIC
ACID
AS
A
PRECURSOR
OF
BIOLOGICALLY
ACTIVE
COMPOUNDS
AND
OTHER
INTERESTING
DERIVATIVES
276
9.2.1
9.2.1.1
9.2.1.2
9.2.1.3
9.2.2
9.2.3
9.2.3.1
9.2.4
9.2.5
9.2.5.1
9.2.5.2
9.2.5.3
9.2.6
9.2.7
9.2.7.1
9.2.7.2
9.2.7.3
9.2.7.4
SYNTHESIS
OF
ENT-HALIMANOLIDES
278
SYNTHESIS
OF
NATURAL
ENT-HALIMANOLIDE
SYNTHESIS
278
SYNTHESIS
OF
A
AND
P-HYDROXYHALIMANOLIDES
280
SYNTHESIS
OF
FURO-ENT-HALIMANOLIDE
280
SYNTHESIS
OF
CHETTAPHANINS
281
SYNTHESIS
OF
SESTERTERPENOLIDES
281
SYNTHESIS
OF
SESTERTERPENOLIDES,
ANALOGUES
OF
DYSIDIOLIDE
282
SYNTHESIS
OF
SESTERTERPENOLIDE
AND
GLYCEROL
HYBRIDS
283
SYNTHESIS
OF
REARRANGED
COMPOUNDS
283
SYNTHESIS
OF
ENT-LABDANES
FROM
ENT-HALIMANES
283
SYNTHESIS
OF
ABEOPICRASANES
FROM
ENT-HALIMANES
284
SYNTHESIS
OF
[4.3.3]PROPELLANES
FROM
ENT-HALIMANES
285
SYNTHESIS
OF
QUINONE/HYDROQUINONE
SESQUITERPENES
285
SYNTHESIS
OF
SESQUI
AND
DITERPENE
ALKALOIDS
286
SYNTHESIS
OF
THE
DITERPENE
ALKALOID,
(+)-AGELASINE
C
287
SYNTHESIS
OF
DITERPENE
ALKALOID,
(+)-THIERSINDOLE
C
288
SYNTHESIS
OF
SESQUITERPENYL
INDOLES
289
SYNTHESIS
OF
SESQUITERPENE
INDOLES,
ANALOGUES
OF
POLYALTHENOL
AND
PENTACYCLINDOLE
289
ACKNOWLEDGMENTS
290
REFERENCES
291
10
ALKALOIDS
AS
CHIRAL
BUILDING
BLOCKS,
AUXILIARIES,
LIGANDS,
AND
MOLECULAR
DIVERSITY
297
KAROL
KACPRZAK,
ELZBIETA
WOJACZYNSKA,
ANDRZEJ
TROCHIMCZUK,
FRANZ
STEPPELER,
AND
JACEK
WOJACZYNSKI
10.1
10.2
10.3
10.4
10.5
10.6
10.7
INTRODUCTION
297
EPHEDRA
ALKALOIDS
303
TOBACCO
ALKALOIDS
(NICOTINE
AND
ANABASINE)
311
LUPIN
ALKALOIDS
314
CINCHONA
ALKALOIDS
325
TROPANE
ALKALOIDS
335
ALKALOIDS
AS
BUILDING
BLOCKS
IN
THE
SYNTHESES
OF
CHIRAL
POLYMERS
AND
THEIR
APPLICATION
338
ACKNOWLEDGMENTS
345
REFERENCES
345
CONTENTS
11
CHIRAL
BUILDING
BLOCKS
FOR
TOTAL
STEROID
SYNTHESIS
AND
THE
USE
OF
STEROIDS
AS
CHIRAL
BUILDING
BLOCKS
IN
ORGANIC
SYNTHESIS
367
IZABELLA
JASTRZ^BSKA
AND
DOUGLAS
F.
COVEY
11.1
11.2
11.2.1
11.2.2
11.2.3
11.2.4
11.2.5
11.2.6
11.2.7
11.2.8
11.2.9
11.3
11.3.1
11.3.2
11.3.3
INTRODUCTION
367
CHIRAL
BUILDING
BLOCKS
FOR
THE
CONSTRUCTION
OF
STEROIDS
368
CHIRAL
BUILDING
BLOCK
1
(CBB
1)
368
CHIRAL
BUILDING
BLOCK
2
(CBB
2)
369
CHIRAL
BUILDING
BLOCK
3
(CBB
3)
370
CHIRAL
BUILDING
BLOCK
4
(CBB
4)
370
CHIRAL
BUILDING
BLOCK
5
(CBB
5)
371
CHIRAL
BUILDING
BLOCK
6
(CBB
6)
372
CHIRAL
BUILDING
BLOCK
7
(CBB
7)
373
CHIRAL
BUILDING
BLOCK
8
(CBB
8)
374
CHIRAL
BUILDING
BLOCK
9
(CBB
9)
375
STEROIDS
AS
CHIRAL
BUILDING
BLOCKS
376
SYNTHESIS
OF
C-NOR-D-HOMO-STEROIDS
376
PREGNENOLONE
AS
A
CHIRAL
BUILDING
BLOCK:
SYNTHESIS
OF
CYCLOCITRINOL
377
4
ANDROSTENE-3,17-DIONE
AS
A
CHIRAL
BUILDING
BLOCK:
SYNTHESIS
OF
VULGAROBUFOTOXIN
377
11.3.4
11.3.4.1
11.3.4.2
11.3.4.3
11.3.4.4
11.3.5
11.3.5.1
11.3.5.2
ERGOSTEROL
AS
A
CHIRAL
BUILDING
BLOCK
378
SYNTHESIS
OF
PLEUROCIN
A/MATSUTAKONE
378
SYNTHESIS
OF
STROPHASTEROL
A
379
SYNTHESIS
OF
HERBARULIDE
379
SYNTHESIS
OF
PINNIGORGIOL
E
AND
PINNIGORGIOL
B
380
TIGOGENIN
AS
A
CHIRAL
BUILDING
BLOCK
381
SYNTHESIS
OF
CLATHSTEROL
381
SYNTHESIS
OF
NORTRITERPENOID
PROPINDILACTONE
G
383
REFERENCES
384
12
CHIRAL
ORGANOPHOSPHORUS
COMPOUNDS
IN
ASYMMETRIC
SYNTHESIS
389
ELZBIETA
LASTAWIECKA,
SYLWIA
SOWA,
KATARZYNA
SZWACZKO,
KAMIL
DZIUBA,
MAREK
STANKEVII,
AND
ADAM
WTODARCZYK
12.1
12.2
INTRODUCTION
389
ORGANOPHOSPHORUS
COMPOUNDS
WITH
INCORPORATED
CHIRAL
TERPENE
MOIETIES
389
12.3
12.4
12.5
ORGANOPHOSPHORUS
COMPOUNDS
WITH
AXIAL
CHIRALITY
397
CHIRAL
AMINOPHOSPHONIC
ACIDS
AND
THEIR
ANALOGS
406
STEREOGENIC
ORGANOPHOSPHORUS
COMPOUNDS
WITH
P
-
N
AND/OR
P
-
0
BONDS
418
12.6
SUMMARY
425
REFERENCES
426
CONTENTS
XI
13
ORGANOSULFUR
COMPOUNDS
AS
CHIRAL
BUILDING
BLOCKS
441
MARIA
A.M.
CAPOZZI
AND
COSIMO
CARDELLICCHIO
13.1
13.2
13.3
13.3.1
13.3.2
13.3.3
13.3.4
13.3.5
13.4
13.4.1
13.4.2
13.5
STATE
OF
THE
ART
441
INTRODUCTION
441
THE
TRADITION
442
MENTHYL
(RS)
OR
(SS)-P-TOLUENESULFINATE
(ANDERSEN
'
S
REAGENT)
442
(R)-P-TOLUENESULFINAMIDE
(DAVIS
'
REAGENT)
449
(IS,
2R,
5S)-MENTHYL
(S)-P-BROMOPHENYLSULFINATE
451
(R)-TERT-BUTHYL
TERT-BUTANETHIOSULFINATE
(ELLMAN
'
S
REAGENT)
452
SULFOXIMINES
454
IDEAS
FOR
THE
FUTURE
454
DAG-CHEMISTRY
454
ARYL
BENZYL
SULFOXIDES
455
CONCLUSIONS
456
REFERENCES
456
14
ORGANOSELENIUM
COMPOUNDS
AS
CHIRAL
BUILDING
BLOCKS
463
LUANA
BAGNOLI
AND
CLAUDIO
SANTI
14.1
14.2
INTRODUCTION
463
ASYMMETRIC
SELENOFUCTIONALIZATION
REACTIONS
PROMOTED
BY
ELECTROPHILIC
SELENIUM
REAGENTS
463
14.3
VINYL
SELENONES
AS
IMPORTANT
BUILDING
BLOCKS
IN
ASYMMETRIC
PROCESSES
470
14.4
ASYMMETRIC
SYNTHESIS
BY
MICHAEL-INITIATED
RING
CLOSURE
REACTIONS
FROM
VINYL
SELENONES
470
14.5
FUNCTIONALIZATION
OF
VINYL
SELENONES
OF
CARBOHYDRATES
AND
NUCLEOTIDES
472
14.6
ASYMMETRIC
ORGANOCATALYTIC
TRANSFORMATIONS
STARTING
WITH
VINYL
SELENONES
475
14.7
CONCLUSION
481
REFERENCES
481
15
ALLENES
AS
CHIRAL
BUILDING
BLOCKS
IN
ASYMMETRIC
SYNTHESIS
489
RAFAT
LOSKA
AND
ALICJA
WASILEWSKA-ROSA
15.1
15.2
15.3
INTRODUCTION
489
NUCLEOPHILIC
ADDITION
AND
SUBSTITUTION
490
ALLENYLZINC
AND
INDIUM
REAGENTS,
ALLENYLSILANES
AND
ALLENYLSTANNANES
491
15.4
15.5
15.6
15.7
EPOXIDATION,
AZIRIDINATION,
AND
SILACYCLOPROPANATION
OF
ALLENES
494
NAZAROV
CYCLIZATION
OF
ALLENYL
VINYL
KETONES
499
NUCLEOPHILIC
CYCLIZATION
AND
ADDITION
PROMOTED
BY
ELECTROPHILES
500
CYCLOISOMERIZATION
AND
OTHER
REACTIONS
CATALYZED
BY
TRANSITION
METALS
510
XII
CONTENTS
15.8
CYCLOADDITION
OF
ALLENES
513
ACKNOWLEDGMENTS
51
7
REFERENCES
517
16
THE
SYNTHESIS
AND
APPLICATION
OF
BINOL
DERIVATIVES
AS
EFFECTIVE
BUILDING
BLOCKS
FOR
CATALYSTS
EMPLOYED
IN
ENANTIOSELECTIVE
SYNTHESIS
523
JANUSZ
JURCZAK,
PATRYK
NIEDBALA,
AND
AGATA
TYSZKA-GUMKOWSKA
16.1
16.2
16.2.1
16.2.2
16.2.3
16.3
16.4
16.4.1
16.4.2
16.4.3
16.4.4
16.4.5
16.4.6
INTRODUCTION
523
BINOL
DERIVATIVES
WITH
FREE
HYDROXYL
GROUPS
524
ALLYLBORATION
REACTIONS
525
CONJUGATED
ADDITION
REACTIONS
526
OTHER
EXAMPLES
526
ONIUM
SALTS AS
CHARGED
CATALYSTS
IN
PTC
529
CHIRAL
PHOSPHORIC
ACIDS
DERIVED
FROM
BINOL
PLATFORM
533
MICHAEL
REACTION
533
FRIEDEL-CRAFTS
REACTION
534
DIELS-ALDER
REACTION
535
1
,3-DIPOLAR
CYCLOADDITION
538
MULTICOMPONENT
REACTIONS
539
OTHER
EXAMPLES
543
ACKNOWLEDGMENTS
544
REFERENCES
545
17
CHIRAL
ACENES:
SYNTHESIS
AND
APPLICATIONS
551
ANDREA
NITTI,
GIOVANNI
PREDA
T
AND
DARIO
PASINI
17.1
17.2
17.2.1
17.2.1.1
17.2.1.2
17.2.1.3
17.2.2
17.2.2.1
17.2.2.2
17.2.2.3
17.2.2.4
17.2.2.5
17.2.3
17.2.4
17.2.4.1
17.2.4.2
17.2.4.3
17.3
17.4
INTRODUCTION
551
CHIRAL
CARBO[N]HELICENES
552
STRUCTURE
AND
PROPERTIES
OF
HELICENES
553
TOPOLOGICAL
DESCRIPTION
553
AROMATICITY
AND
OPTOELECTRONIC
PROPERTIES
554
CHIRALITY
OF
HELICENE
557
RACEMIC
SYNTHESIS
AND
OPTICAL
RESOLUTION
METHODS
559
METAL-FREE
PHOTOCYCLIZATION
REACTIONS
559
DIELS-ALDER
CYCLOADDITION
560
FRIEDEL-CRAFTS-TYPE
CYCLIZATION
560
METAL-CATALYZED
REACTIONS
561
OPTICAL
RESOLUTION
564
ASYMMETRIC
SYNTHESES
565
APPLICATION OF
CHIRAL
CARBO[N]HELICENES
567
HELICENES
IN
CATALYSIS
567
HELICENES
IN
ORGANIC
ELECTRONICS
569
HELICENES
IN
BIOCHEMISTRY
571
TWISTACENES
571
CHIRAL
NANOBELTS
572
INDEX
653
CONTENTS
|
XIII
17.5
CONCLUDING
REMARKS
575
REFERENCES
575
18
2-AZA-21-CARBAPORPHYRIN
IN
CONSTRUCTION
OF
CHIRAL
SUPRAMOLECULAR
ASSEMBLIES
583
SEBASTIAN
KONIARZ
AND
PIOTR
J.
CHMIELEWSKI
18.1
18.2
18.2.1
18.2.2
18.3
18.3.1
18.3.2
18.4
PREFACE
583
MONOMERS
586
FREE
BASES
586
METAL
COMPLEXES
596
DIMERS
AND
OLIGOMERS
601
COORDINATING
OLIGOMERS
602
COVALENTLY
LINKED
DIMERS
606
SUMMARY
AND
OUTLOOK
611
REFERENCES
612
19
CATENANE,
ROTAXANE,
AND
MOLECULAR
KNOT
CHIRAL
BUILDING
BLOCKS
623
JEAN-CLAUDE
CHAMBRON
19.1
19.2
19.3
19.4
19.5
19.6
19.6.1
19.6.2
19.6.3
19.6.3.1
19.6.3.2
19.7
INTRODUCTION
623
ELEMENTS
OF
MOLECULAR
TOPOLOGY
624
TOPOLOGICAL
CHIRALITY
AND
CHIRAL
CATENANES
627
CHIRAL
[2]ROTAXANES
631
TOPOLOGICALLY
CHIRAL
MOLECULAR
KNOTS
634
CATENANES,
ROTAXANES,
AND
KNOTS
AS
CHIRAL
BUILDING
BLOCKS
638
CATENANES
639
ROTAXANES
639
MOLECULAR
KNOTS
642
COVALENT
LINKING
OF
TREFOIL
KNOT
BUILDING
BLOCKS
642
COMPOSITE
KNOTS
644
CONCLUSIONS
648
REFERENCES
650 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author2 | Wojaczyńska, Elżbieta Wojaczyński, Jacek |
| author2_role | edt edt |
| author2_variant | e w ew j w jw |
| author_GND | (DE-588)1271039168 |
| author_facet | Wojaczyńska, Elżbieta Wojaczyński, Jacek |
| building | Verbundindex |
| bvnumber | BV048489176 |
| classification_rvk | VK 5800 VK 5500 |
| ctrlnum | (OCoLC)1349539825 (DE-599)DNB1253682518 |
| discipline | Chemie / Pharmazie |
| discipline_str_mv | Chemie / Pharmazie |
| format | Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>02635nam a22006498c 4500</leader><controlfield tag="001">BV048489176</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">20230322 </controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">220927s2022 gw a||| |||| 00||| eng d</controlfield><datafield tag="015" ind1=" " ind2=" "><subfield code="a">22,N12</subfield><subfield code="2">dnb</subfield></datafield><datafield tag="016" ind1="7" ind2=" "><subfield code="a">1253682518</subfield><subfield code="2">DE-101</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">9783527349463</subfield><subfield code="c">hbk.</subfield><subfield code="9">978-3-527-34946-3</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(OCoLC)1349539825</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)DNB1253682518</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-604</subfield><subfield code="b">ger</subfield><subfield code="e">rda</subfield></datafield><datafield tag="041" ind1="0" ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="044" ind1=" " ind2=" "><subfield code="a">gw</subfield><subfield code="c">XA-DE-BW</subfield></datafield><datafield tag="049" ind1=" " ind2=" "><subfield code="a">DE-29T</subfield><subfield code="a">DE-83</subfield><subfield code="a">DE-703</subfield><subfield code="a">DE-11</subfield><subfield code="a">DE-19</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">VK 5800</subfield><subfield code="0">(DE-625)147412:253</subfield><subfield code="2">rvk</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">VK 5500</subfield><subfield code="0">(DE-625)147401:253</subfield><subfield code="2">rvk</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="8">1\p</subfield><subfield code="a">540</subfield><subfield code="2">23sdnb</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Chiral building blocks in asymmetric synthesis</subfield><subfield code="b">synthesis and applications</subfield><subfield code="c">edited by Elżbieta Wojaczyńska, Jacek Wojaczyński</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="a">Weinheim</subfield><subfield code="b">Wiley-VCH</subfield><subfield code="c">[2022]</subfield></datafield><datafield tag="264" ind1=" " ind2="4"><subfield code="c">© 2022</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">xx, 668 Seiten</subfield><subfield code="b">Illustrationen, Diagramme</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Asymmetrische Synthese</subfield><subfield code="0">(DE-588)4135603-2</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Chirale Verbindungen</subfield><subfield code="0">(DE-588)4348527-3</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Asymmetrische Synthese</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">CH30: Technische u. Industrielle Chemie</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">CH40: Katalyse</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">CH81: Organische Chemie / Methoden, Synthesen, Verfahren</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Catalysis</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Chemie</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Chemische Synthese</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Chemistry</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Industrial Chemistry</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Katalyse</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Methods - Synthesis & Techniques</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Organische Chemie / Methoden, Synthesen, Verfahren</subfield></datafield><datafield tag="653" ind1=" " ind2=" "><subfield code="a">Technische u. Industrielle Chemie</subfield></datafield><datafield tag="655" ind1=" " ind2="7"><subfield code="0">(DE-588)4143413-4</subfield><subfield code="a">Aufsatzsammlung</subfield><subfield code="2">gnd-content</subfield></datafield><datafield tag="689" ind1="0" ind2="0"><subfield code="a">Asymmetrische Synthese</subfield><subfield code="0">(DE-588)4135603-2</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="1"><subfield code="a">Chirale Verbindungen</subfield><subfield code="0">(DE-588)4348527-3</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Wojaczyńska, Elżbieta</subfield><subfield code="0">(DE-588)1271039168</subfield><subfield code="4">edt</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Wojaczyński, Jacek</subfield><subfield code="4">edt</subfield></datafield><datafield tag="710" ind1="2" ind2=" "><subfield code="a">Wiley-VCH</subfield><subfield code="0">(DE-588)16179388-5</subfield><subfield code="4">pbl</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, PDF</subfield><subfield code="z">978-3-527-83418-1</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, EPUB</subfield><subfield code="z">978-3-527-83419-8</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe, oBook</subfield><subfield code="z">978-3-527-83420-4</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">DNB Datenaustausch</subfield><subfield code="q">application/pdf</subfield><subfield code="u">http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033866684&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="999" ind1=" " ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-033866684</subfield></datafield><datafield tag="883" ind1="1" ind2=" "><subfield code="8">1\p</subfield><subfield code="a">vlb</subfield><subfield code="d">20220318</subfield><subfield code="q">DE-101</subfield><subfield code="u">https://d-nb.info/provenance/plan#vlb</subfield></datafield></record></collection> |
| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV048489176 |
| illustrated | Illustrated |
| index_date | 2024-07-03T20:41:11Z |
| indexdate | 2024-07-10T09:39:30Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527349463 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-033866684 |
| oclc_num | 1349539825 |
| open_access_boolean | |
| owner | DE-29T DE-83 DE-703 DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-29T DE-83 DE-703 DE-11 DE-19 DE-BY-UBM |
| physical | xx, 668 Seiten Illustrationen, Diagramme |
| publishDate | 2022 |
| publishDateSearch | 2022 |
| publishDateSort | 2022 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Chiral building blocks in asymmetric synthesis synthesis and applications edited by Elżbieta Wojaczyńska, Jacek Wojaczyński Weinheim Wiley-VCH [2022] © 2022 xx, 668 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Chirale Verbindungen (DE-588)4348527-3 gnd rswk-swf Asymmetrische Synthese CH30: Technische u. Industrielle Chemie CH40: Katalyse CH81: Organische Chemie / Methoden, Synthesen, Verfahren Catalysis Chemie Chemische Synthese Chemistry Industrial Chemistry Katalyse Methods - Synthesis & Techniques Organische Chemie / Methoden, Synthesen, Verfahren Technische u. Industrielle Chemie (DE-588)4143413-4 Aufsatzsammlung gnd-content Asymmetrische Synthese (DE-588)4135603-2 s Chirale Verbindungen (DE-588)4348527-3 s DE-604 Wojaczyńska, Elżbieta (DE-588)1271039168 edt Wojaczyński, Jacek edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-83418-1 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-83419-8 Erscheint auch als Online-Ausgabe, oBook 978-3-527-83420-4 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033866684&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p vlb 20220318 DE-101 https://d-nb.info/provenance/plan#vlb |
| spellingShingle | Chiral building blocks in asymmetric synthesis synthesis and applications Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| subject_GND | (DE-588)4135603-2 (DE-588)4348527-3 (DE-588)4143413-4 |
| title | Chiral building blocks in asymmetric synthesis synthesis and applications |
| title_auth | Chiral building blocks in asymmetric synthesis synthesis and applications |
| title_exact_search | Chiral building blocks in asymmetric synthesis synthesis and applications |
| title_exact_search_txtP | Chiral building blocks in asymmetric synthesis synthesis and applications |
| title_full | Chiral building blocks in asymmetric synthesis synthesis and applications edited by Elżbieta Wojaczyńska, Jacek Wojaczyński |
| title_fullStr | Chiral building blocks in asymmetric synthesis synthesis and applications edited by Elżbieta Wojaczyńska, Jacek Wojaczyński |
| title_full_unstemmed | Chiral building blocks in asymmetric synthesis synthesis and applications edited by Elżbieta Wojaczyńska, Jacek Wojaczyński |
| title_short | Chiral building blocks in asymmetric synthesis |
| title_sort | chiral building blocks in asymmetric synthesis synthesis and applications |
| title_sub | synthesis and applications |
| topic | Asymmetrische Synthese (DE-588)4135603-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| topic_facet | Asymmetrische Synthese Chirale Verbindungen Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033866684&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wojaczynskaelzbieta chiralbuildingblocksinasymmetricsynthesissynthesisandapplications AT wojaczynskijacek chiralbuildingblocksinasymmetricsynthesissynthesisandapplications AT wileyvch chiralbuildingblocksinasymmetricsynthesissynthesisandapplications |