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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.
The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis (more than 1300 references), the aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions. It is important to note that the references were each individually checked by the authors to verify relevance to the topics under discussion. The study of stereoselectivity has evolved from issues of diastereoselectivity, through auxiliary-based methods for the synthesis of enantiomerically pure compounds (diastereoselectivity followed by separation and auxiliary cleavage), to asymmetric catalysis. In the latter instance, enantiomers (not diastereomers) are the products, and highly selective reactions and modern purification techniques allow preparation - in a single step - of chiral substances in 99% ee for many reaction types. After an explanation of the basic physical-organic principles of stereoselectivity, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Analytical Methods" provides a critical overview of the most common methods for analysis of stereoisomers. The authors then follow the 'tried-and-true' format of grouping the material by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions (enolate alkylations, organometal additions to carbonyls, aldol and Michael reactions, and cycloadditions and rearrangements), one chapter on reductions and hydroborations (carbon-hydrogen bond forming reactions), and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). Leading references are provided to natural product synthesis that have been accomplished using a given reaction as a key step. In addition to tables of examples that show high selectivity, a transition state analysis is presented to explain - to the current level of understanding - the stereoselectivity of each reaction. In one case (Cram's rule) the evolution of the current theory is detailed from its first tentative (1952) postulate to the current Felkin-Anh-Heathcock formalism. For other reactions, only the currently accepted rationale is presented. Examination of these rationales also exposes the weaknesses of current theories, in that they cannot always explain the experimental observations. These shortcomings provide a challenge for future mechanistic investigations.
The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. In references, Topics in Organometallic Chemistry is abbreviated as Top Organomet Chem and cited as a journal.
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.
Praise for the previous editions "An excellent text . . . will no doubt provide the benchmark for comparative works for many years." —Journal of the American Chemical Society "An excellent state-of-the-art compilation of catalytic asymmetric chemistry . . . should be included in any chemistry reference collection." —Choice "This is a tremendous resource and an excellent read. I recommend immediate purchase." —Perkin Transactions Since this important work was first published in 1993, the field of catalytic asymmetric synthesis has grown explosively, spawning effective new methods for obtaining enantiomerically pure compounds on a large scale and stimulating new applications in diverse fields—from medicine to materials science. Catalytic Asymmetric Synthesis, Third Edition addresses these rapid changes through contributions from highly recognized world leaders in the field. This seminal text presents detailed accounts of the most important catalytic asymmetric reactions known today, and discusses recent advances and essential information on the initial development of certain processes. An excellent working resource for academic researchers and industrial chemists alike, the Third Edition features: Six entirely new chapters focusing on novel approaches to catalytic asymmetric synthesis including non-conventional media/conditions, organocatalysis, chiral Lewis and Bronsted acids, CH activation, carbon-heteroatom bond-forming reactions, and enzyme-catalyzed asymmetric synthesis A new section focusing on the important new reaction, asymmetric metathesis, in carbon-carbon bond-forming reactions Updated chapters on hydrogenation, carbon-carbon bond-forming reactions, hydrosilylations, carbonylations, oxidations, amplifications and autocatalysis, and polymerization reactions Retaining the best of its predecessors but now thoroughly up to date, Catalytic Asymmetric Synthesis, Third Edition serves as an excellent desktop reference and text for researchers and students from the upper-level undergraduates through experienced professionals in industry or academia.
The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis, this book presents a detailed analysis of the factors that govern stereoselectivity in organic reactions. After an explanation of the basic physical-organic principles governing stereoselective reactions, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Practical Aspects of Asymmetric Synthesis" provides a critical overview of the most common methods for the preparation of enantiomerically pure compounds, techniques for analysis of stereoisomers using chromatographic, spectroscopic, and chiroptical methods. The authors then present an overview of the most important methods in contemporary asymmetric synthesis organized by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions, one chapter on reductions, and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). This organization allows the reader to compare the leading methods for asymmetric synthesis in an appropriate context. A highlight of the book is the presentation and discussion of transition states at the current level of understanding, for important reaction types. In addition, extensive tables of examples are used to give the reader an appreciation for the scope of each reaction. Finally, leading references are provided to natural product synthesis that has been accomplished using a given reaction as a key step. - Authoritative glossary to aid understanding of stereochemical terminology - Explanations of the key factors influencing stereoselectivity with numerous examples, organized by reaction type - A handy reference guide to the literature of asymmetric synthesis for practitioners in the field
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!
A comprehensive overview of fundamental concepts of asymmetric synthesis along with in-depth discussion. Recent developments that address important synthetic challenges are presented and highlighted with hundreds of examples.
Chemical industries have to face the challenge of finding adequate processes to produce large quantities of new products, while at the same time decreasing both the impact on the environment and the risk of disaster. This book addresses this challenge. It discusses the problems of environmentally benign organic processes on an interdisciplinary approach. The book features experts in selective catalysis, development of new reagents and methods who present their recent results.
A reactions oriented course is a staple of most graduate organic programs, and synthesis is taught either as a part of that course or as a special topic. Ideally, the incoming student is an organic major, who has a good working knowledge of basic reactions, stereochemistry and conformational principles. In fact, however, many (often most) of the students in a first year graduate level organic course have deficiencies in their undergraduate work, are not organic majors and are not synthetically inclined. To save students much time catching up this text provides a reliable and readily available source for background material that will enable all graduate students to reach the same high level of proficiency in organic chemistry. Produced over many years with extensive feedback from students taking an organic chemistry course this book provides a reaction based approach. The first two chapters provide an introduction to functional groups; these are followed by chapters reviewing basic organic transformations (e.g. oxidation, reduction). The book then looks at carbon-carbon bond formation reactions and ways to 'disconnect' a bigger molecule into simpler building blocks. Most chapters include an extensive list of questions to test the reader's understanding. There is also a new chapter outlining full retrosynthetic analyses of complex molecules which highlights common problems made by scientists. The book is intended for graduate and postgraduate students, scientific researchers in chemistry - New publisher, new edition; extensively updated and corrected - Over 950 new references with more than 6100 references in total - Over 600 new reactions and figures replaced or updated - Over 300 new homework problems from the current literature to provide nearly 800 problems to test reader understanding of the key principles