Organolithiums: Selectivity for Synthesis (Volume 23) (Tetrahedron Organic Chemistry, Volume 23)

Whilst research into organolithium compounds has been ongoing for the past 15 years little is known about organolithium products of ortholithiation reactions. This volume contains an up-to-date survey of organolithiums and their use in synthesis. 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 Content: Foreword Page xi Jonathan Clayden Acknowledgements Page xiii Abbreviations Pages xv-xvi Chapter 1 Introduction Original Research Article Pages 1-8 Chapter 2 Regioselective synthesis of organolithiums by deprotonation Original Research Article Pages 9-109 Chapter 3 Regioselective synthesis of organolithiums by X-Li exchange Original Research Article Pages 111-147 Chapter 4 Regioselective synthesis of organolithiums by C-X reduction Original Research Article Pages 149-168 Chapter 5 Stereoselective and stereospecific synthesis of organolithiums Original Research Article Pages 169-240 Chapter 6 Stereoselective and stereospecific substitution reactions of organolithiums Original Research Article Pages 241-271 Chapter 7 Regio- and stereoselective addition reactions of organolithiums Original Research Article Pages 273-335 Chapter 8 Organolithium rearrangements Original Research Article Pages 337-364 Chapter 9 Organolithiums in synthesis Original Research Article Pages 365-375 Index Pages 377-383 Organolithiums (with the exceptions of methyllithium and phenyllithium) are remarkably soluble even in hydrocarbon solvents, and simple organolithium starting materials are available as stable hydrocarbon solutions (Table 1.2.1). Jonathan Clayden. Includes Bibliographical References And Index.