Conjugate Addition Reactions In Organic Synthesis

This book provides an introduction to the chemistry of conjugate reactions, a group of reactions that constitute one of the most important classes of chemical reactions in organic synthesis. The book is organised in terms of the major classes of conjugate acceptors. Within each of these classes, the chemistry and applications of conjugate additions with several different categories of nucleophiles have been examined. Where several different nucleophiles achieve the same synthetic transformation, they are cross-referenced within the book and qualitative comparisons offered where appropriate. Examples of the use of conjugate additions in total synthesis of important molecules are included, with a special emphasis throughout the book on stereoselectivity. This will be a useful main text for graduate and postgraduate courses on conjugate addition reactions or the Michael reaction. It could also serve as a supplementary text for courses on topics such as the chemistry of organocopper reagents, enamines and carbanion chemistry.

This book, unique in its field, is a comprehensive description of all the methodologies reported for carrying out conjugate addition reactions in a stereoselective way, using small chiral organic molecules as catalysts (organocatalysts). In the last 3-4 years, this has been a rapidly growing field in organic chemistry, and many papers have appeared reporting excellent protocols for carrying out these highly efficient transformations that compete well with other classical approachse using transition metal catalysts. A particularly attractive feature of this transformation relies upon the fact that the conjugate addition (Michael and Hetero-Michael reactions) is an extraoridinarily effective means to initiate cascade processes which result in the formation of complex molecules from very small and simple starting blocks. The book, written by noted experts, covers all recent advances in this not topic, and provides a good state-of-the-art review for organic chemists working in this field and all those who wish to start projects in this area. The Series is intended to provide an accessible reference for postgraduates and industrialists working in the field of catalysis and its applications. Books will be produced either as monographs or reference handbooks. The Series will cover research developments and applications of catalysis, in both academia and industry.

Textbook on modern methods of organic synthesis.

Conjugate Addition Reactions in Organic Synthesis, second edition, provides an introduction to the chemistry of conjugate reactions, a group of reactions that constitute one of the most important classes of chemical reactions in organic synthesis. The book is organized according to class of acceptor rather than the class of nucleophile, which makes for easier synthetic problem solving. All aspects of conjugate addition reactions are covered, including theory, mechanism, catalysis, and total synthesis. Asymmetric processes are featured heavily, and there is emphasis on catalysis, given its importance in all aspects of organic synthesis today. Extensive examples in total synthesis illustrate how particular synthetic challenges are addressed and resolved with conjugate addition chemistry. The second edition features new coverage of acceptors and nucleophiles, as well as organocatalysis, gold catalysis, peptide catalysis, arene additions, and emerging areas such as biocatalytic methods and advances in mechanism theory. This book is an ideal reference for advanced undergraduates, post-graduates, researchers, and academics working in medicinal, pharmaceutical, polymer and industrial chemistry. Features a unique structure for this subject which enables readers to readily access information based on specific classes of conjugate acceptor Provides a thorough account of the latest thinking of the mechanistic basis of conjugate addition reactions and all the latest - and best - methods for achieving the highest selectivity in conjugate addition reactions Includes over 200 examples of total synthesis illustrating how particular synthetic challenges are addressed and resolved with conjugate addition chemistry Covers an up to date treatment of the latest aspects of conjugate addition reactions including inter alia, cascade reactions, organocatalysis and flow chemistry

This thesis is concerned with the asymmetric conjugate addition reactions of a range of chiral nucloeophiles. Chapter 1 introduces the conjugate addition reaction as a valuable carbon-carbon and carbon-heteroatom bond forming reaction in organic chemistry, and explores the asymmet- ric conjugate addition of a range of chiral and achiral carbon and nitrogen nucleophiles to a range of acceptors. Chapter 2 explores the use of the N-benzyl-N-([alpha]-methylbenzyl)amino group as a chi- ral auxiliary, by employing the attempted conjugate additions of both N-benzyl-N-([alpha]- methylbenzyl)hydrazine and N -benzyl-N -([alpha]-methylbenzyl)hydroxylamine as chiral ammo- nia and water equivalents respectively. Chapter 3 describes the asymmetric and stereoselective preparation of a range of 4,4- disubstituted isoxazolidin-5-ones from the conjugate addition of lithium (S)-N-tert-butyl- dimethylsilyloxy-N -([alpha]-methylbenzyl)amide. The isoxazolidin-5-ones are then globally de- protected via hydrogenolysis, giving rise to the corresponding [beta]2,2,3-amino acids. Chapter 4 focuses on the development of a protocol to effect the conjugate addition of a chiral aniline equivalent. The scope of the reaction is delineated by varying both the nu- cleophile and the [alpha],[beta]-unsaturated ester. Finally, cyclisation of the [beta]-N-arylamino esters to the corresponding tetrahydroquinolines is explored, and an application to the synthesis of the natural product (-)-angustureine is presented. Chapter 5 contains full experimental procedures and characterisation data for all com- pounds synthesised in Chapters 2, 3 and 4.

This Volume covers the formation of carbon-carbon single-, double- and triple bonds by substitution and addition reactions as well as by various rearrangements. The formation of carbon-carbon multiple bonds by elimination and condensation procedures is fully documented. In addition the synthesis of carbon-hydrogen bonds principally by substitution and addition reactions is featured as is the preparation of a wide variety of carbon-centred anions, cations and radicals.

A best-selling mechanistic organic chemistry text in Germany, this text's translation into English fills a long-existing need for a modern, thorough and accessible treatment of reaction mechanisms for students of organic chemistry at the advanced undergraduate and graduate level. Knowledge of reaction mechanisms is essential to all applied areas of organic chemistry; this text fulfills that need by presenting the right material at the right level.

The second edition of Comprehensive Organic Synthesis—winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers—builds upon the highly respected first edition in drawing together the new common themes that underlie the many disparate areas of organic chemistry. These themes support effective and efficient synthetic strategies, thus providing a comprehensive overview of this important discipline. Fully revised and updated, this new set forms an essential reference work for all those seeking information on the solution of synthetic problems, whether they are experienced practitioners or chemists whose major interests lie outside organic synthesis. In addition, synthetic chemists requiring the essential facts in new areas, as well as students completely new to the field, will find Comprehensive Organic Synthesis, Second Edition an invaluable source, providing an authoritative overview of core concepts. Winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers Contains more than170 articles across nine volumes, including detailed analysis of core topics such as bonds, oxidation, and reduction Includes more than10,000 schemes and images Fully revised and updated; important growth areas—including combinatorial chemistry, new technological, industrial, and green chemistry developments—are covered extensively

Organozinc reagents are used extensively in organic synthesis to find useful pathways to organic products. Illustrated and tabulated with over 950 equations, schemes, tables, and figures, Organozinc Reagents in Organic Synthesis provides an overall picture of the chemistry of organozinc compounds. Written by a professor of organic chemistry, the book familiarizes the reader with the reactions involving organozinc reagents that have general usefulness in synthesis. Emphasis is placed on preparation methods and reactivity of organozinc reagents. Reactions are summarized in equations and schemes, making it easy for you to see the characteristics of each type of reaction.

Copper in organic synthesis has seen a tremendous development over the past ten years. This text represents the most comprehensive survey on the use of Copper and Cuprates in organic synthesis. The first time that the Patai Series touches on Copper compounds, it contains contributions by leading experts, and delivers the quality expected from the Patai Series.

The last two decades have seen a rapid growth in the synthetic processing of both simple and complex molecules, aimed at meeting the needs of society in all aspects of life. Many efforts have been devoted to the development of new biologically active compounds, new materials with innovative properties such as bio-compatibility, new catalysts that allow highly selective transformations, and technologies that facilitate the synthetic pro cesses. This book is a compendium of recent progress in all these aspects of synthetic chemistry. It collects the lectures of the XII International Conference on Organic Synthesis, held in Venice from June 28 to July 2, 1998, in which the present state of art of this discipline has been reported. The topics covered include: combinatorial chemistry, new synthetic methods, stereo selective synthesis, metal-mediated synthesis, and target oriented synthesis. The book collects the contributions, in the mentioned topics, of 43 scientists from 19 different countries. The contributions presented in the Conference as plenary lectures are reported in the first section of the book. Particular attention has been dedicated to combinatorial chemistry, a new and promising methodology for the synthesis of libraries of pharmaco logically interesting compounds in order to allow the automatic pharmacological screening of thousands of compounds. The Conference has dedicated to combinatorial chemistry a mini-symposium in which scientists from academy and companies have described the current trends of this very new technology.

A complete overview covering the application of metal-based chiral Lewis acids from all parts of the periodic table, the Author emphasizes the most recent contributions to the field as well as prominent direction of development. The book discusses the design of chiral complexes as well as a wide spectrum of reactions promoted by various chiral Lewis acids, including water-compatible acids as well as the most important applications in the chemical and pharmaceutical industries. A must-have for catalytic and organic chemists working in the field, both in academia and industry, as well as pharmaceutical and medicinal chemists.

This unique and long-awaited handbook on this important topic in the hot field of stereoselective organic synthesis covers several types of nucleophiles. Top international authors deal with modern forms of achieving stereoselective conjugate additions based on the use of chiral auxiliaries or asymmetric catalysis, such as P-N ligands, organocatalysis, domino reactions, Lewis acid and base catalysis. There is also a discussion of the employment of enantioselective conjugate addition transformations in total synthesis of important molecules. With its reliable and previously unpublished experimental procedures, this is a true source of high quality information.

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.

This book bridges the gap between sophomore and advanced / graduate level organic chemistry courses, providing students with a necessary background to begin research in either an industry or academic environment. • Covers key concepts that include retrosynthesis, conformational analysis, and functional group transformations as well as presents the latest developments in organometallic chemistry and C–C bond formation • Uses a concise and easy-to-read style, with many illustrated examples • Updates material, examples, and references from the first edition • Adds coverage of organocatalysts and organometallic reagents

“Much of life can be understood in rational terms if expressed in the language of chemistry. It is an international language, a language without dialects, a language for all time, a language that explains where we came from, what we are, and where the physical world will allow us to go. Chemical Language has great esthetic beauty and links the physical sciences to the b- logical sciences. ” from The Two Cultures: Chemistry and Biology by Arthur Kornberg (Nobel Prize in Physiology and Medicine, 1959) Over the past two centuries, chemistry has evolved from a relatively pure disciplinary pursuit to a position of central importance in the physical and life sciences. More generally, it has p- vided the language and methodology that has unified, integrated and, indeed, molecularized the sciences, shaping our understanding of the molecular world and in so doing the direction, development and destiny of scientific research. The “language of chemistry” referred to by my former Stanford colleague is made up of atoms and bonds and their interactions. It is a s- tem of knowledge that allows us to understand structure and events at a molecular level and increasingly to use that understanding to create new knowledge and beneficial change. The words on this page, for example, are detected by the eye in a series of events, now generally understood at the molecular level.

C-H, C-O, C-C, and C-Heteroatom bond forming processes by using metal-ligand approaches for the synthesis of organic compounds of biological, pharmacological and organic nanotechnological utility are the key areas addressed in this book. Authored by a European team of leaders in the field, it brings together innovative approaches for a variety of catalysis reactions and processes frequently applied in organic synthesis into a handy reference work. It covers all major types of catalysis, including homogeneous, heterogeneous, and organocatalysis, as well as mechanistic and computational studies. Special attention is paid to the improvements in efficiency and sustainability of important catalytic processes, such as selective oxidations, hydrogenation, and cross-coupling reactions, and to their utilization in industry. The result is a valuable resource for advanced researchers in both academia and industry, as well as graduate students in organic chemistry aiming for chemo-, regio- or stereoselective synthesis of organic compounds by using novel catalytic systems.

Organic Syntheses Based on Name Reactions.

This book provides the reader with an illustrative overview concerning successful and widely used applications of organocatalysis in the field of natural product synthesis. The main focus will be on organocatalytic key-steps for each (multi-step) synthesis described, whereas other often particularly innovative transformations will be omitted, as this would be beyond the scope of this volume.

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