Organolithiums: Selectivity for Synthesis: Selectivity for Synthesis
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Table of contents
- Table of Contentsv
- Forewordxi
- Acknowledgementsxiii
- Abbreviationsxv
- CHAPTER 1. Introduction1
- 1.1 Scope and overview1
- 1.2 Organolithiums in solution2
- References7
- CHAPTER 2. Regioselective Synthesis of Organolithiums by Deprotonation9
- 2.1 General points9
- 2.2 Lithiation α a to heteroatoms10
- 2.3 Ortholithiation28
- 2.4 Lateral lithiation73
- 2.5 Remote lithiation, and β-1ithiation of non-aromatic compounds86
- 2.6 Superbases87
- 2.7 Cooperation, competition and regioselectivity90
- References96
- CHAPTER 3. Regioselective Synthesis of Organolithiums by X-Li Exchange111
- 3.1 Halogen-lithium exchange111
- 3.2 Tin-lithium exchange136
- 3.3 Chalcogen-lithium exchange139
- 3.4 Phosphorus-lithium exchange142
- References142
- CHAPTER 4. Regioselective Synthesis of Organolithiums by C-X Reduction149
- 4.1 Reductive lithiation of alkyl and aryl halides149
- 4.2 Reductive lithiation of C–O bonds154
- 4.3 Reductive lithiation of C–N bonds158
- 4.4 Reductive lithiation of C–S bonds159
- 4.5 Reductive lithiation of C–C bonds and n-bonds165
- References165
- CHAPTER 5. Stereoselective and Stereospecific Synthesis of Organolithiums169
- 5.1 Configurational stability of organolithiums169
- 5.2 Stereospecific synthesis of organolithiums by X–Li exchange214
- 5.3 Diastereoselective deprotonation224
- 5.4 Enantioselective deprotonation226
- References235
- CHAPTER 6. Stereospecific and Stereoselective Substitution Reactions of Organolithiums241
- 6.1 Stereospecific reactions of organolithium compounds241
- 6.2 Stereoselective substitution in the presence of chiral ligands258
- References269
- CHAPTER 7. Regio- and Stereoselective Addition Reactions of Organolithiums273
- 7.1 Intermolecular addition to π bonds: Carbolithiation273
- 7.2 Intramolecular addition and substitution reactions: anionic cyclisation282
- References329
- CHAPTER 8. Organolithium Rearrangements337
- 8.1 Shapiro Reaction337
- 8.2 Brook Rearrangements340
- 8.3 [ 1,2]-Wittig Rearrangements346
- 8.4 [2,3]-Wittig Rearrangements351
- References360
- CHAPTER 9. Organolithiums in Synthesis365
- 9.1 Ochratoxin: ortholithiation and anionic Fries rearrangement365
- 9.2 Corydalic acid methyl ester: lateral lithiation366
- 9.3 Fredericamycin A: ortho, lateral and α-lithiation367
- 9.4 (+)-Atpenin B: metallation of an aromatic heterocycle369
- 9.5 Flurbiprofen: metallation with LiCKOR superbases370
- 9.6 California Red Scale Pheromone: α- and reductive lithiation371
- 9.7 C1-C9 of the Bryostatins: diastereoselective bromine-lithium exchange372
- 9.8 (S)-1-Methyldodecyl acetate, a Drosophila pheromone: (-)-sparteine assisted enantioselective lit373
- 9.9 (–)-Paroxetine: (–)-sparteine-promoted asymmetric lithiation and substitution374
- References375
- INDEX377
Organolithiums: Selectivity for Synthesis