Superbases for organic synthesis: guanidines, amidines and phosphazenes and related organocatalysts
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Hoboken
Wiley
2009
|
| Ausgabe: | 1. publ. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Includes bibliographical references and index |
| Beschreibung: | XIV, 326 S. graph. Darst. |
| ISBN: | 9780470518007 |
Internformat
MARC
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| 003 | DE-604 | ||
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| 008 | 090204s2009 xxud||| |||| 00||| eng d | ||
| 010 | |a 2008044058 | ||
| 020 | |a 9780470518007 |c cloth : alk. paper |9 978-0-470-51800-7 | ||
| 035 | |a (OCoLC)317075507 | ||
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| 100 | 1 | |a Ishikawa, Tsutomu |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Superbases for organic synthesis |b guanidines, amidines and phosphazenes and related organocatalysts |c Tsutomu Ishikawa |
| 250 | |a 1. publ. | ||
| 264 | 1 | |a Hoboken |b Wiley |c 2009 | |
| 300 | |a XIV, 326 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Includes bibliographical references and index | ||
| 650 | 4 | |a Amidines | |
| 650 | 4 | |a Guanidines | |
| 650 | 4 | |a Phosphazo compounds | |
| 650 | 4 | |a Organic bases | |
| 650 | 0 | 7 | |a Guanidinderivate |0 (DE-588)4158492-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Phosphazene |0 (DE-588)4174373-8 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Katalyse |0 (DE-588)4029921-1 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Base |0 (DE-588)4144090-0 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Amidine |0 (DE-588)4195247-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Organische Synthese |0 (DE-588)4075695-6 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Phosphazene |0 (DE-588)4174373-8 |D s |
| 689 | 0 | 1 | |a Amidine |0 (DE-588)4195247-9 |D s |
| 689 | 0 | 2 | |a Guanidinderivate |0 (DE-588)4158492-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 689 | 1 | 0 | |a Base |0 (DE-588)4144090-0 |D s |
| 689 | 1 | 1 | |a Katalyse |0 (DE-588)4029921-1 |D s |
| 689 | 1 | 2 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 1 | |8 1\p |5 DE-604 | |
| 856 | 4 | 2 | |m Digitalisierung UB Bayreuth |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017095079&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-017095079 | ||
| 883 | 1 | |8 1\p |a cgwrk |d 20201028 |q DE-101 |u https://d-nb.info/provenance/plan#cgwrk | |
Datensatz im Suchindex
| _version_ | 1804138586280296448 |
|---|---|
| adam_text | Contents
Preface
xiii
Acknowledgements
xv
Contributors
xvii
1.
General Aspects of Organosuperbases
1
Tsutomu Ishikawa
Reterences
2.
Physico-Chemical Properties of Organosuperbases
6
9
Davor
Margetic
2.1
Introduction
9
2.2
Proton Sponges
10
2.2.1
Classical Proton Sponges
10
2.2.2
Proton Sponges with Other Aromatic Backbones
12
2.2.3
Polycyclic Proton Sponges
14
2.3
Amidines
20
2.4
Guanidines
24
2.5
Phosphazenes
31
2.6
Guanidinophosphazenes
35
2.7
Other Phosphorus Containing
Superbases: Verkade s
Proazaphosphatranes
37
2.8
Theoretical Methods
41
2.9
Concluding Remarks
41
References
42
3.
Amidines in Organic Synthesis
49
Tsutomu Ishikawa and Takuya Kumamoto
49
52
52
53
53
54
59
3.1
Introduction
3.2
Preparation of Amidines
3.2.1
Alkylation of Amidines
3.2.2
Condensation of 1,2-Diamine
3.2.3
Coupling of Imines (Isoamarine Synthesis)
3.2.4
Modification of Amide Derivatives
3.2.5
Multi-Component Reaction
viii Contents
3.2.6
Oxidative Amidination
62
3.2.7
Oxidative Cyclization
to Bisamidine
63
3.2.8
Ring Opening of
Aziridine
63
3.3
Application
of Amidines to
Organic
Synthesis
65
3.3.1
Acetoxybromination
65
3.3.2
Aldol-Like Reaction
66
3.3.3
Azidation
67
3.3.4
Aziridination
68
3.3.5
Baylis-Hillman Reaction
68
3.3.6
Cycloaddition
68
3.3.7
Dehydrohalogenation
70
3.3.8
Deprotection
70
3.3.9
Deprotonation
71
3.3.10
Displacement Reaction
72
3.3.11
Horner-Wadsworth-Emmons Reaction
72
3.3.12
Intramolecular
Cyclization 72
3.3.13
Isomerization
72
3.3.14
Metal-Mediated Reaction
74
3.3.15
Michael Reaction
77
3.3.16
Nef
Reaction
78
3.3.17
Nucleophilic Epoxidation
79
3.3.18
Oxidation
80
3.3.19
Pudovik-phospha-Brook Rearrangement
80
3.3.20
[1,4]-Silyl Transfer
80
3.3.21
Tandem Reaction
81
3.4
Amidinium Salts: Design and Synthesis
82
3.4.1
Catalyst
82
3.4.2
Molecular Recognition
82
3.4.3
Reagent Source
85
3.5
Concluding Remarks
86
References
86
4.
Guanidines in Organic Synthesis
93
Tsutomu Ishikawa
4.1.
Introduction
93
4.2.
Preparation of Chiral Guanidines
94
4.2.1
Polysubstituted Acyclic and Monocyclic Guanidines
95
4.2.2
Monosubstituted Guanidines (Guanidinylation)
95
4.2.3
Bicyclic Guanidines
97
4.2.4
Preparation Based on DMC Chemistry
98
4.3
Guanidines as Synthetic Tools
99
4.3.1
Addition
99
4.3.2
Substitution
112
4.3.3
Others
117
4.4
Guanidinium Salt
125
Contents ix
4.4.1 Guanidinium Ylide 125
4.4.2
Ionic
Liquid 128
4.4.3 Tetramethylguanidinium Azide (TMGA) 131
4.5
Concluding Remarks
136
References
136
5. Phosphazene:
Preparation, Reaction and Catalytic Role
145
Yoshinori Kondo
5.1
Introduction
145
5.2
Deprotonative Transformations Using Stoichiometric
Phosphazenes
150
5.2.1
Use of PI Base
151
5.2.2
Use of P2 Base
156
5.2.3
Use of P4 Base
159
5.2.4
Use of P5 Base
164
5.3
Transformation Using Phosphazene Catalyst
164
5.3.1
Addition of Nucleophiles to Alkyne
164
5.3.2
Catalytic Activation of Silylated Nucleophiles
165
5.4
Proazaphosphatrane Base (Verkade s Base)
176
5.4.1
Properties of Proazaphosphatrane
176
5.4.2
Synthesis Using Proazaphosphatrane
176
5.5
Concluding Remarks
181
References
181
6.
Polymer-Supported Organosuperbases
187
Hiyoshizo Kotsuki
6.1
Introduction
187
188
190
198
200
205
205
211
211
211
211
215
217
220
225
225
6.2
Acylation Reactions
6.3
Alkylation Reactions
6.4
Heterocyclization
6.5
Miscellaneous
6.6
Concluding Remarks
References
7.
Application of Organosuperbases to Total Synthesis
Kazuo Nagasawa
7.1
Introduction
7.2
Carbon-Carbon Bond Forming Reactions
7.2.1
Aldol Reaction
7.2.2
Michael Reaction
7.2.3
Pericyclic Reaction
7.2.4 Wittig
Reaction
7.3
Deprotection
7.4
Elimination
χ
Contents
7.5
Ether Synthesis
230
7.6
Heteroatom
Conjugate
Addition
233
7.7
Isomerization
237
7.8
Concluding
Remarks
247
References
247
8.
Related Organocatalysts
(1):
A Proton
Sponge
251
Kazuo Nagasawa
8.1
Introduction
251
8.2
Alkylation and
Hetero
Michael Reaction
252
8.2.1
Amine
Synthesis by N-Alkylation
252
8.2.2
Ether Synthesis by O-Alkylation
252
8.3
Amide Formation
256
8.4
Carbon-Carbon Bond Forming Reaction
259
8.4.1
Alkylation and
Nitro Aldol
Reaction
259
8.4.2
Pericyclic Reaction
261
8.5
Palladium Catalyzed Reaction
264
8.6
Concluding Remarks
268
References
268
9.
Related Organocatalysts
(2):
Urea Derivatives
273
Waka Nakanishi
9.1
Introduction
273
9.2 Bisphenol
as an Organoacid Catalyst
274
9.2.1
Role of Phenol as Hydrogen Donor
274
9.2.2 Bisphenol
Catalysed Reaction
276
9.3
Urea and Thiourea as Achiral Catalysts
277
9.3.1
Role of Urea and Thiourea as Hydrogen Donors
277
9.3.2
Urea and Thiourea Catalysed Reactions
278
9.4
Urea and Thiourea as Chiral Catalysts
282
9.4.1
Monothiourea Catalysts
284
9.4.2
Bisthiourea Catalysts
289
9.4.3
Urea-Sulfinimide Hybrid Catalyst
290
9.5
Concluding Remarks
291
References
292
10.
Amidines and Guanidines in Natural Products and Medicines
295
Takuya Kumamoto
10.1
Introduction
295
10.2
Natural Amidine Derivatives
295
10.2.1
Natural Amidines from Microorganisms and Fungi
296
10.2.2
Natural Amidines from Marine Invertebrates
298
10.2.3
Natural Amidines from Higher Plants
299
10.3
Natural Guanidine Derivatives
299
10.3.1
Natural Guanidines from Microorganisms
300
Contents
xi
10.3.2
Natural Guanidines
from Marine Invertebrates
301
10.3.3
Natural Guanidines from Higher Plant
302
10.4
Medicinal Amidine and Guanidine Derivatives
303
10.4.1
Biguanides
305
10.4.2
Cimetidine
305
10.4.3
Imipenem
306
10.4.4
NOS
Inhibitors
307
10.4.5
Pentamidine
307
References
308
11.
Perspectives
315
Tsutomu Ishikawa and
Davor
Margetic
References
319
Index
321
|
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| discipline | Chemie / Pharmazie Chemie |
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| id | DE-604.BV035290000 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T21:30:32Z |
| institution | BVB |
| isbn | 9780470518007 |
| language | English |
| lccn | 2008044058 |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-017095079 |
| oclc_num | 317075507 |
| open_access_boolean | |
| owner | DE-703 DE-91G DE-BY-TUM DE-11 |
| owner_facet | DE-703 DE-91G DE-BY-TUM DE-11 |
| physical | XIV, 326 S. graph. Darst. |
| publishDate | 2009 |
| publishDateSearch | 2009 |
| publishDateSort | 2009 |
| publisher | Wiley |
| record_format | marc |
| spelling | Ishikawa, Tsutomu Verfasser aut Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts Tsutomu Ishikawa 1. publ. Hoboken Wiley 2009 XIV, 326 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Includes bibliographical references and index Amidines Guanidines Phosphazo compounds Organic bases Guanidinderivate (DE-588)4158492-2 gnd rswk-swf Phosphazene (DE-588)4174373-8 gnd rswk-swf Katalyse (DE-588)4029921-1 gnd rswk-swf Base (DE-588)4144090-0 gnd rswk-swf Amidine (DE-588)4195247-9 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Phosphazene (DE-588)4174373-8 s Amidine (DE-588)4195247-9 s Guanidinderivate (DE-588)4158492-2 s DE-604 Base (DE-588)4144090-0 s Katalyse (DE-588)4029921-1 s Organische Synthese (DE-588)4075695-6 s 1\p DE-604 Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017095079&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Ishikawa, Tsutomu Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts Amidines Guanidines Phosphazo compounds Organic bases Guanidinderivate (DE-588)4158492-2 gnd Phosphazene (DE-588)4174373-8 gnd Katalyse (DE-588)4029921-1 gnd Base (DE-588)4144090-0 gnd Amidine (DE-588)4195247-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4158492-2 (DE-588)4174373-8 (DE-588)4029921-1 (DE-588)4144090-0 (DE-588)4195247-9 (DE-588)4075695-6 |
| title | Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts |
| title_auth | Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts |
| title_exact_search | Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts |
| title_full | Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts Tsutomu Ishikawa |
| title_fullStr | Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts Tsutomu Ishikawa |
| title_full_unstemmed | Superbases for organic synthesis guanidines, amidines and phosphazenes and related organocatalysts Tsutomu Ishikawa |
| title_short | Superbases for organic synthesis |
| title_sort | superbases for organic synthesis guanidines amidines and phosphazenes and related organocatalysts |
| title_sub | guanidines, amidines and phosphazenes and related organocatalysts |
| topic | Amidines Guanidines Phosphazo compounds Organic bases Guanidinderivate (DE-588)4158492-2 gnd Phosphazene (DE-588)4174373-8 gnd Katalyse (DE-588)4029921-1 gnd Base (DE-588)4144090-0 gnd Amidine (DE-588)4195247-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Amidines Guanidines Phosphazo compounds Organic bases Guanidinderivate Phosphazene Katalyse Base Amidine Organische Synthese |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017095079&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT ishikawatsutomu superbasesfororganicsynthesisguanidinesamidinesandphosphazenesandrelatedorganocatalysts |