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Organolithiums: Selectivity for Synthesis
 
 

Organolithiums: Selectivity for Synthesis, 1st Edition

 
Organolithiums: Selectivity for Synthesis, 1st Edition,Jonathan Clayden,ISBN9780080432625
 
 
 

  

Pergamon

9780080432625

9780080538167

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Jonathan Clayden

Affiliations and Expertise

Department of Chemistry University of Manchester Manchester UK

Organolithiums: Selectivity for Synthesis, 1st Edition

  • 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 Reaction13
    • 8.2 Brook Rearrangements1921
    • 8.3 [1,2]-Wittig Rearrangements6466
    • 8.4 [2,3]-Wittig Rearrangements9092
  • Chapter 9: Organolithiums in Synthesis
    • 9.1 Ochratoxin: ortholithiation and anionic ortho-Fries rearrangement1
    • 9.2 Corydalic acid methyl ester: lateral lithiation2
    • 9.3 Fredericamycin A: ortho, lateral and α-lithiation3
    • 9.4 (±)-Atpenin B: lithiation of an aromatic heterocycle4
    • 9.5 Flurbiprofen: metallation with LiCKOR superbases5
    • 9.6 California Red Scale Pheromone: α- and reductive lithiation6
    • 9.7 C1-C9 of the Bryostatins: diastereoselective bromine-lithium exchange7
    • 9.8 (S)-1-Methyldodecyl acetate, a Drosophila pheromone: (−)-sparteine assisted enantioselective lithiation8
    • 9.9 (−)-Paroxetine: (−)-sparteine-promoted asymmetric lithiation and substitution9
  • Index
    • Publisher Summary
 
 
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