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The ASI workshop on "Selectivities in Lewis Acid Promoted Reactions" held in the Emmantina-Hotel in Athens-Glyfada, Greece, October 2-7, 1988 was held to bring some light into the darkness of Lewis acid induced processes. As such the workshop reflects some current trends in organic synthesis, where Lewis acids are becoming a powerful tool in many different modern reactions, e.g. Diels-Alder reactions, Ene reactions, Sakurai reactions, and in general silicon and tin chemistry. The objective of this meeting was to bring together most of the world experts in the field to discuss the major reactions promoted by Lewis acids. Organic synthesis will play a major role in this book connected with some fundamental mechanistic work on allylsilane and -tin chemistry. Both natural product synthesis and unnatural molecules are presented in the chapters. The book presents all the 15 invited lectures and the contributions of 15 posters. I am confident that the material presented in this book will stimulate the chemistry, which has been discussed on our meeting, around the world. The meeting and the book were only possible through a grant of the NATO Scientific Affairs Devision and financial support by the following companies: Kali Chemie (Hannover, W-Germany), E. Merck (Darmstadt, W-Germany), Sandoz (Basel, Switzerland), Schering (Berlin, W-Germany).
The Diels-Alder reaction has long been a powerful tool in organic synthesis. In recent years, the Alder ene reaction has also achieved some prominence. From the beginning, it was apparent that the intramolecular variants of these reactions would be feasible. Many such have been reported, but the results are widely scattered in the chemical literature. This volume is an attempt to synthesize results observed to date, and to suggest directions for future development. One of the limiting factors in the application of the intramolecular Diels Alder reaction has been the development of methods for the preparation of the requisite trienes. The fIrst chapter of this volume summarizes methods for the preparation of dienes and dienophiles. Examples representative of every general approach to 1,3-dienes and to dienophilic functional group combinations have been included. There are two questions one might ask in considering the prospective cyclization of a given triene: what are the factors that govern the rate of cyclization? and, for cyclizations that lead to the creation of one or more new chiral centers, what are the factors that govern diastereoselectivity? These questions are addressed in Chapter Two. The third chapter is devoted to the all-carbon intramolecular Alder ene reaction. The tables in that chapter summarize all examples that could be found in the literature through 1981, with several additional examples from 1982. Leading references to heterocyclic ene reactions are also included in this chapter.
The practical aspects of Lewis acid-assisted stereoselective synthesis, basic principles of Lewis-acid catalysis, stereoisomerism, chemical selectivity and stereoselectivity are the focus of this work. It is aimed at organic-synthetic professionals employing stereoselective Lewis acid catalysts, who wish to increase their understanding and odds of successful outcomes. Intended for researchers, graduate-level or advanced undergrads with a thorough grasp of the fundamentals of synthetic organic chemistry. This is not a textbook thus the reader is freed from pedagogical restrictions. Various areas of Lewis acid catalysis and stereochemistry are selected for recent significant developments. The interplay of structure and reactivity within innovative mechanistic constructs is always involved, and mechanistic models are included when particularly valuable for understanding or predicting observed stereoselectivity. When a detailed mechanistic description is provided, the author has opted not to alter the proposal by the original investigator when no new data requiring its modification is available. The chapters are organized by concepts rather than reaction types.
Lewis acids provide inexpensive access to elaborated molecules obtained with high selectivities (regio-, stereo-, and enantioselectivity). Lewis Acids and Selectivity in Organic Synthesis is the first book to deal with these new and promising roles of Lewis acids. The book begins with general considerations on Lewis acids and a description of Lewis acid-carbonyl complexes, which are involved in most of the reactions described: ene reactions, allylsilane and allyltin addition to carbonyl compounds, addition of nucleophiles to acetals, conjugated addition of allylsilanes and allyltins to unsaturated carbonyl compounds (Sakurai reaction), and Diels-Alder reaction. Subsequent chapters examine these issue in detail, with special attention given to the way Lewis acids induce diastereo- and enantioselectivity. The extensive use of schemes (approximately 1000) ensures rapid visual uptake of the information. Lewis Acids and Selectivity in Organic Synthesis serves as a valuable source of information for all who face the challenge of selectivity in organic synthesis.
Provides the background, tools, and models required to understand organic synthesis and plan chemical reactions more efficiently Knowledge of physical chemistry is essential for achieving successful chemical reactions in organic chemistry. Chemists must be competent in a range of areas to understand organic synthesis. Organic Chemistry provides the methods, models, and tools necessary to fully comprehend organic reactions. Written by two internationally recognized experts in the field, this much-needed textbook fills a gap in current literature on physical organic chemistry. Rigorous yet straightforward chapters first examine chemical equilibria, thermodynamics, reaction rates and mechanisms, and molecular orbital theory, providing readers with a strong foundation in physical organic chemistry. Subsequent chapters demonstrate various reactions involving organic, organometallic, and biochemical reactants and catalysts. Throughout the text, numerous questions and exercises, over 800 in total, help readers strengthen their comprehension of the subject and highlight key points of learning. The companion Organic Chemistry Workbook contains complete references and answers to every question in this text. A much-needed resource for students and working chemists alike, this text: -Presents models that establish if a reaction is possible, estimate how long it will take, and determine its properties -Describes reactions with broad practical value in synthesis and biology, such as C-C-coupling reactions, pericyclic reactions, and catalytic reactions -Enables readers to plan chemical reactions more efficiently -Features clear illustrations, figures, and tables -With a Foreword by Nobel Prize Laureate Robert H. Grubbs Organic Chemistry: Theory, Reactivity, and Mechanisms in Modern Synthesis is an ideal textbook for students and instructors of chemistry, and a valuable work of reference for organic chemists, physical chemists, and chemical engineers.
The state-of-the-art in stereoselective synthesis! Thoroughly revised and updated, this enlarged second edition offers a plethora of valuable information on methods and reagents in stereoselective synthesis. Methods have been selected for high efficiency and selectivity; mechanistic aspects are treated succinctly, with a strong emphasis on practical applications. For this new edition, material has been added on * homogeneous diastereoselective hydrogenations * enantioselective oxidations * novel, efficient chiral auxiliaries Much of the information given is presented in figures and tables, which makes the book a valuable reference work for the practically minded organic chemist. From reviews of the first edition: 'The extensive material in the volume should prove particularly useful to anyone involved in synthetic chemistry or teaching a course in organic chemistry.' Journal of Medicinal Chemistry 'With nearly 1400 references cited, the book contains a wealth of information and should be a useful addition to the chemist's library.' The American Scientist
The only book series to summarize the latest progress on organic reaction mechanisms, Organic Reaction Mechanisms, 1984 surveys the development in understanding of the main classes of organic reaction mechanisms reported in the primary scientific literature in 1984. The 20th annual volume in this highly successful series highlights mechanisms of stereo-specific reactions. Reviews are compiled by a team of experienced editors and authors, allowing advanced undergraduates, graduate students, postdocs, and chemists to rely on the volume's continuing quality of selection and presentation.
This three-volume set represents the first comprehensive coverage of the rapidly expanding field of Lewis base catalysis that has attracted enormous attention in recent years. Lewis base catalysis is a conceptually novel paradigm that encompasses an extremely wide variety of preparatively useful transformations and is particularly effective for enantioselectively constructing new stereogenic centers. As electron-pair donors, Lewis bases can influence the rate and stereochemical course of myriad synthetic organic reactions. The book presents the conceptual/mechanistic principles that underlie Lewis base catalysis, and then builds upon that foundation with a thorough presentation of many different reaction types. And last but not least, the editors, Prof. Edwin Vedejs and Prof. Scott E. Denmark, are without doubt the leaders in this emerging field and have compiled high quality contributions from an impressive collection of international experts.