Organolithiums Selectivity For Synthesis

Organolithiums: Selectivity for 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.

This volume is the first dedicated to a comprehensive coverage of this rapidly developing transdisciplinary field. It provides a rich source of essential information on synthesizing molecules in an enantioselective manner using organolithiums, and serves as an inspiration for future developments.

This unique book covers fundamentals of organolithium compounds and gives a comprehensive overview of the latest synthetic advances and developments in the field. Part I covers computational and spectroscopic aspects as well as structure-reactivity relationships of organolithiums, whereas Part II deals with new lithium-based synthetic methodologies as well as novel synthetic applications of functionalized lithium compounds. A useful resource for newcomers and active researchers involved in organic synthesis, whether working in academia or industry!

Volume 4 focuses on additions and the resulting substitutions at carbon-carbon &pgr;-bonds. Part 1 includes processes generally considered as simple polar reactions, reactive electrophiles and nucleophiles adding to alkenes and alkynes. A major topic is Michael-type addition to electron deficient &pgr;-bonds, featured in the first six chapters. In part 2 are collected the four general processes leading to nucleophilic aromatic substitution, including radical chain processes and transition metal activation through to &pgr;-complexation. Metal-activated addition (generally by nucleophiles) to alkenes and polyenes is presented in part 3, including allylic alkylation catalyzed by palladium. The coverage of nonpolar additions in part 4 includes radical additions, organometal addition (Heck reaction), carbene addition, and 1,3-dipolar cycloadditions.

Topics in Stereochemistry, previously edited by "the father of stereochemistry" Ernest L. Eliel, is a longstanding, successful series covering the most important advances in the field. The much-anticipated Volume 26 on stereochemical aspects of organolithium compounds includes chapters on the following topics: * Asymmetric Deprotonations Using Chiral Lithium Amide Bases * Self-Regeneration of Stereocenters (SRS) via Stereolabile Axially Chiral Intermediates * Overview of Carbanion Dynamics and Electrophilic Substitutions in Chiral Organolithium Compounds * Oxiranyllithiums as Chiral Synthons for Asymmetric Synthesis * Test on the Configurational Stability/Lability of Organolithium Compounds * Mechanism and Stereochemical Features in Asymmetric Deprotonation Using RLi/(-)-Sparteine Bases * Dynamic Resolutions of Chiral Organolithiums Volume 26 of Topics in Stereochemistry marks the end of an era, while developing a bridge to the next generation. A new generation in publishing, parallel to a new generation in Stereochemistry mandated a new venue and modus operandi for Topics. Zurich, the home of Werner and Wislicenus, has a unique heritage in Stereochemistry. Fortunately, the Wiley family's publishing partnerships include Verlag Helvetica Chimica Acta, a house with a reputation for superior quality in publishing. Indeed, within the pages of its namesake periodical, Helvetica Chimica Acta, one finds many of the seminal research works of stereochemistry's giants. As such, a transfer of editorial operations to Zurich and a collaboration bringing Topics as a series closer to periodical status provides a growth platform for the future.

This volume presents an account of the applications of organolithium compounds in synthesis. General considerations, such as solvents, inert atmospheres, apparatus and safety, are discussed as well as detailed specific methods.

Selectivity is an important part of organic synthesis. The whole basis of organic chemistry, and especially organic synthesis, depends upon the selectivity which can be achieved in organic reactions. This concise textbook describes the strategies which can be adopted to improve selectivity, and the reactions which have been specially designed to afford high selectivity. The book illustrates the range of processes to which these principles can be applied and the high degree of selectivity which can be achieved. Selectivity in Organic Synthesis provides a solid introduction to this subject, focusing on the key areas and applications. Selectivity in Organic Synthesis features: * A concise introduction to selectivity in organic chemistry. * Lucidly written text including many carefully chosen examples and applications. * Numerous problems along with their solutions to help and encourage the reader. Suitable for organic chemistry students taking a course on organic synthesis or asymmetric synthesis in the 3rd or final year of an undergraduate chemistry course or in the first year of a postgraduate course.