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Table Of Contents

General Aspects of Organosuperbases
Physico-Chemical Properties of Organosuperbases
2.1 Introduction
2.2 Proton Sponges
2.2.1 ‘Classical’ Proton Sponges
2.2.2 Proton Sponges with Other Aromatic Backbones
2.2.3 Polycyclic Proton Sponges
2.3 Amidines
2.4 Guanidines
2.5 Phosphazenes
2.6 Guanidinophosphazenes
2.8 Theoretical Methods
2.9 Concluding Remarks
References
Amidines in Organic Synthesis
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
3.2.6 Oxidative Amidination
3.2.7 Oxidative Cyclization to Bisamidine
3.2.8 Ring Opening of Aziridine
3.3 Application of Amidines to Organic Synthesis
3.3.1 Acetoxybromination
3.3.2 Aldol-Like Reaction
3.3.3 Azidation
3.3.4 Aziridination
3.3.5 Baylis–Hillman Reaction
3.3.6 Cycloaddition
3.3.7 Dehydrohalogenation
3.3.8 Deprotection
3.3.9 Deprotonation
3.3.10 Displacement Reaction
3.3.11 Horner–Wadsworth–Emmons Reaction
3.3.12 Intramolecular Cyclization
3.3.13 Isomerization
3.3.14 Metal-Mediated Reaction
3.3.15 Michael Reaction
3.3.16 Nef Reaction
3.3.17 Nucleophilic Epoxidation
3.3.18 Oxidation
3.3.19 Pudovik-phospha-Brook Rearrangement
3.3.20 [1,4]-Silyl Transfer
3.3.21 Tandem Reaction
3.4 Amidinium Salts: Design and Synthesis
3.4.1 Catalyst
3.4.2 Molecular Recognition
3.4.3 Reagent Source
3.5 Concluding Remarks
Guanidines in Organic Synthesis
4.1 Introduction
4.2 Preparation of Chiral Guanidines
4.2.1 Polysubstituted Acyclic and Monocyclic Guanidines
4.2.2 Monosubstituted Guanidines (Guanidinylation)
4.3.1 Addition
4.3.2 Substitution
4.3.3 Others
4.4 Guanidinium Salt
4.4.1 Guanidinium Ylide
4.4.2 Ionic Liquid
4.4.3 Tetramethylguanidinium Azide (TMGA)
4.5 Concluding Remarks
Phosphazene: Preparation, Reaction and Catalytic Role
5.1 Introduction
5.2.1 Use of P1 Base
5.2.2 Use of P2 Base
5.2.3 Use of P4 Base
5.2.4 Use of P5 Base
5.3 Transformation Using Phosphazene Catalyst
5.3.1 Addition of Nucleophiles to Alkyne
5.3.2 Catalytic Activation of Silylated Nucleophiles
5.4.2 Synthesis Using Proazaphosphatrane
5.5 Concluding Remarks
6.3 Alkylation Reactions
6.4 Heterocyclization
6.5 Miscellaneous
6.6 Concluding Remarks
Application of Organosuperbases to Total Synthesis
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
7.5 Ether Synthesis
7.6 Heteroatom Conjugate Addition
7.7 Isomerization
7.8 Concluding Remarks
Related Organocatalysts (1): A Proton Sponge
8.1 Introduction
8.2 Alkylation and Hetero Michael Reaction
8.2.1 Amine Synthesis by N-Alkylation
8.2.2 Ether Synthesis by O-Alkylation
8.3 Amide Formation
8.4 Carbon–Carbon Bond Forming Reaction
8.4.1 Alkylation and Nitro Aldol Reaction
8.4.2 Pericyclic Reaction
8.6 Concluding Remarks
Related Organocatalysts (2): Urea Derivatives
9.1 Introduction
9.2 Bisphenol as an Organoacid Catalyst
9.2.1 Role of Phenol as Hydrogen Donor
9.2.2 Bisphenol Catalysed Reaction
9.3 Urea and Thiourea as Achiral Catalysts
9.3.1 Role of Urea and Thiourea as Hydrogen Donors
9.3.2 Urea and Thiourea Catalysed Reactions
9.4 Urea and Thiourea as Chiral Catalysts
9.4.1 Monothiourea Catalysts
9.4.2 Bisthiourea Catalysts
9.4.3 Urea-Sulfinimide Hybrid Catalyst
9.5 Concluding Remarks
Amidines and Guanidines in Natural Products and Medicines
10.1 Introduction
10.2 Natural Amidine Derivatives
10.2.1 Natural Amidines from Microorganisms and Fungi
10.2.2 Natural Amidines from Marine Invertebrates
10.2.3 Natural Amidines from Higher Plants
10.3 Natural Guanidine Derivatives
10.3.1 Natural Guanidines from Microorganisms
P. 1
Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts

Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts

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Published by Wiley
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 modification, possible recyclability, and reduced or zero toxicity. Importantly, these molecules can be derived as natural products – valuable as scientists move towards “sustainable chemistry”, where reagents and catalysts are derived from biomaterial sources.

Superbases for Organic Synthesis is an essential guide to these important molecules for preparative organic synthesis. Topics covered include the following aspects:

an introduction to organosuperbases physicochemical properties of organic superbases amidines and guanidines in organic synthesis phosphazene: preparation, reaction and catalytic role polymer-supported organosuperbases application of organosuperbases to total synthesis related organocatalysts: proton sponges and urea derivatives amidines and guanidines in natural products and medicines

Superbases for Organic Synthesis is a comprehensive, authoritative and up-to-date guide to these important reagents for organic chemists, drug discovery researchers and those interested in the chemistry of natural products.

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 modification, possible recyclability, and reduced or zero toxicity. Importantly, these molecules can be derived as natural products – valuable as scientists move towards “sustainable chemistry”, where reagents and catalysts are derived from biomaterial sources.

Superbases for Organic Synthesis is an essential guide to these important molecules for preparative organic synthesis. Topics covered include the following aspects:

an introduction to organosuperbases physicochemical properties of organic superbases amidines and guanidines in organic synthesis phosphazene: preparation, reaction and catalytic role polymer-supported organosuperbases application of organosuperbases to total synthesis related organocatalysts: proton sponges and urea derivatives amidines and guanidines in natural products and medicines

Superbases for Organic Synthesis is a comprehensive, authoritative and up-to-date guide to these important reagents for organic chemists, drug discovery researchers and those interested in the chemistry of natural products.

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Publish date: Jan 26, 2009
Added to Scribd: Jun 16, 2013
Copyright:Traditional Copyright: All rights reservedISBN:9780470740866
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