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Organolithiums: Selectivity for Synthesis
1st Edition, Volume 23 - July 1, 2002
Author: Jonathan Clayden
Language: English
Hardback ISBN:9780080432625
9 7 8 - 0 - 0 8 - 0 4 3 2 6 2 - 5
eBook ISBN:9780080538167
9 7 8 - 0 - 0 8 - 0 5 3 8 1 6 - 7
This volume, number 23 in the "Tetrahedron Organic Chemistry" series, presents organolithium chemistry from the perspective of a synthetic organic chemist, drawing from the sy…Read more
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This volume, number 23 in the "Tetrahedron Organic Chemistry" series, presents organolithium chemistry from the perspective of a synthetic organic chemist, drawing from the synthetic literature to present a unified overview of how organolithiums can be used to make molecules. The development of methods for the regioselective synthesis of organolithiums has replaced their image of indiscriminate high reactivity with one of controllable and subtle selectivity. Organolithium chemistry has a central role in the selective construction of C-C bonds in both simple and complex molecules, and for example has arguably overtaken aromatic electrophilic substitution as the most powerful method for regioselective functionalisation of aromatic rings. The twin themes of reactivity and selectivity run through the book, which reviews the ways by which organolithiums may be formed and the ways in which they react. Topics include advances in directed metallation, reductive lithiation and organolithium cyclisation reactions, along with a discussion of organolithium stereochemistry and the role played by ligands such as (-)-sparteine.
Foreword
Acknowledgements
Publisher Summary
Abbreviations
Publisher Summary
Chapter 1: Introduction
1.1 Scope and Overview
1.2 Organolithiums in solution
Chapter 2: Regioselective Synthesis of Organolithiums by Deprotonation
2.1 General points
2.2 Lithiation α to heteroatoms
2.3 Ortholithiation
2.4 Lateral Lithiation
2.5 Remote lithiation, and β-lithiation of non-aromatic compounds
2.6 Superbases435
2.7 Cooperation, competition and regioselectivity
Chapter 3: Regioselective Synthesis of Organolithiums by X-Li Exchange
3.1 Halogen-lithium exchange
3.2 Tin-lithium exchange
3.3 Chalcogen-lithium exchange
3.4 Phosphorus-lithium exchange
Chapter 4: Regioselective Synthesis of Organolithiums by C–X Reduction
4.1 Reductive lithiation of alkyl and aryl halides
4.2 Reductive lithiation of C–O bonds9
4.3 Reductive lithiation of C–N bonds
4.4 Reductive lithiation of C–S bonds
4.5 Reductive lithiation of C–C bonds and π-bonds
Chapter 5: Stereoselective and Stereospecific Synthesis of Organolithiums
5.1 Configurational Stability of Organolithiums
5.2 Stereospecific synthesis of organolithiums by X-Li exchange
5.3 Diastereoselective deprotonation
5.4 Enantioselective Deprotonation
Chapter 6: Stereoselective and Stereospecific Substitution Reactions of Organolithiums
6.1 Stereospecific reactions of organolithium compounds
6.2 Stereoselective substitution in the presence of chiral ligands
Chapter 7: Regio- and Stereoselective Addition Reactions of Organolithiums
7.1 Intermolecular addition to π bonds: Carbolithiation
7.2 Intramolecular addition and substitution reactions: anionic cyclisation
Chapter 8: Organolithium Rearrangements
8.1 Shapiro Reaction1–3
8.2 Brook Rearrangements19–21
8.3 [1,2]-Wittig Rearrangements64–66
8.4 [2,3]-Wittig Rearrangements90–92
Chapter 9: Organolithiums in Synthesis
9.1 Ochratoxin: ortholithiation and anionic ortho-Fries rearrangement1