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Preface xiii
Acknowledgements xv
Contributors xvii
1 General Aspects of Organosuperbases Tsutomu Ishikawa 1
References 6
2 Physico-Chemical Properties of Organosuperbases Davor Margetic 9
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 Tsutomu Ishikawa Takuya Kumamoto 49
3.1 Introduction 49
3.2 Preparation of Amidines 52
3.2.1 Alkylation of Amidines 52
3.2.2 Condensation of 1,2-Diamine 53
3.2.3 Coupling of Imines (Isoamarine Synthesis) 53
3.2.4 Modification of Amide Derivatives 54
3.2.5 Multi-Component Reaction 59
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 Rearrangement80
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 Tsutomu Ishikawa 93
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
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 Yoshinori Kondo 145
5.1 Introduction 145
5.2 Deprotonative Transformation Using Stoichiometric Phosphazenes 150
5.2.1 Use of P1 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 Hiyoshizo Kotsuki 187
6.1 Introduction 187
6.2 Acylation Reactions 188
6.3 Alkylation Reactions 190
6.4 Heterocyclization 198
6.5 Miscellaneous 200
6.6 Concluding Remarks 205
References 205
7 Application of Organosuperbases to Total Synthesis Kazuo Nagasawa 211
7.1 Introduction 211
7.2 Carbon-Carbon Bond Forming Reactions 211
7.2.1 Aldol Reaction 211
7.2.2 Michael Reaction 215
7.2.3 Pericyclic Reaction 217
7.2.4 Wittig Reaction 220
7.3 Deprotection 225
7.4 Elimination 225
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 Kazuo Nagasawa 251
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 Waka Nakanishi 273
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 Takuya Kumamoto 295
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
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 Tsutomu Ishikawa Davor Margetic 315
References 319
Index 321
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Robert Stevens
reviewed Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts on January 09, 2013
Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts
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Add Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts, Guanidines, amidines and phosphazenes have been attracting attention in organic synthesis due to their potential functionality resulting from their extremely strong basicity. They are also promising catalysts because of their potential for easy molecular , Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts to the inventory that you are selling on WonderClubX
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Add Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts, Guanidines, amidines and phosphazenes have been attracting attention in organic synthesis due to their potential functionality resulting from their extremely strong basicity. They are also promising catalysts because of their potential for easy molecular , Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts to your collection on WonderClub |
