Solid-Phase Organic Synthesis

Linker design is an expanding field with an exciting future in state-of-the-art organic synthesis. Ever-increasing numbers of ambitious solution phase reactions are being adapted for solid-phase organic chemistry and to accommodate them, large numbers of sophisticated linker units have been developed and are now routinely employed in solid-phase synthesis. Linker Strategies in Solid-Phase Organic Synthesis guides the reader through the evolution of linker units from their genesis in solid-supported peptide chemistry to the cutting edge diversity linker units that are defining a new era of solid phase synthesis. Individual linker classes are covered in easy to follow chapters written by international experts in their respective fields and offer a comprehensive guide to linker technology whilst simultaneously serving as a handbook of synthetic transformations now possible on solid supports. Topics include: the principles of solid phase organic synthesis electrophile and nucleophile cleavable linker units cyclative cleavage as a solid phase strategy photocleavable linker units safety-catch linker units enzyme cleavable linker units T1 and T2 –versatile triazene linker groups hydrazone linker units benzotriazole linker units phosphorus linker units sulfur linker units selenium and tellurium linker units sulfur, oxygen and selenium linker units cleaved by radical processes silicon and germanium linker units boron and stannane linker units bismuth linker units transition metal carbonyl linker units linkers releasing olefins or cycloolefins by ring-closing metathesis fluorous linker units solid-phase radiochemistry The book concludes with extensive linker selection tables, cataloguing the linker units described in this book according to the substrate liberated upon cleavage and conditions used to achieve such cleavage, enabling readers to choose the right linker unit for their synthesis. Linker Strategies in Solid-Phase Organic Synthesis is an essential guide to the diversity of linker units for organic chemists in academia and industry working in the broad areas of solid-phase organic synthesis and diversity oriented synthesis, medicinal chemists in the pharmaceutical industry who routinely employ solid-phase chemistry in the drug discovery business, and advanced undergraduates, postgraduates, and organic chemists with an interest in leading-edge developments in their field.

Presents both the fundamental concepts and the most recent applications in solid-phase organic synthesis With its emphasis on basic concepts, Solid-Phase Organic Synthesis guides readers through all the steps needed to design and perform successful solid-phase organic syntheses. The authors focus on the fundamentals of heterogeneous supports in the synthesis of organic molecules, explaining the use of a solid material to facilitate organic synthesis. This comprehensive text not only presents the fundamentals, but also reviews the most recent research findings and applications, offering readers everything needed to conduct their own state-of-the-art science experiments. Featuring chapters written by leading researchers in the field, Solid-Phase Organic Synthesis is divided into two parts: Part One, Concepts and Strategies, discusses the linker groups used to attach the synthesis substrate to the solid support, colorimetric tests to identify the presence of functional groups, combinatorial synthesis, and diversity-oriented synthesis. Readers will discover how solid-phase synthesis is currently used to facilitate the discovery of new molecular functionality. The final chapter discusses how using a support can change or increase reaction selectivity. Part Two, Applications, presents examples of the solid-phase synthesis of various classes of organic molecules. Chapters explore general asymmetric synthesis on a support, strategies for heterocyclic synthesis, and synthesis of radioactive organic molecules, dyes, dendrimers, and oligosaccharides. Each chapter ends with a set of conclusions that underscore the key concepts and methods. References in each chapter enable readers to investigate any topic in greater depth. With its presentation of basic concepts as well as recent findings and applications, Solid-Phase Organic Synthesis is the ideal starting point for students and researchers in organic, medicinal, and combinatorial chemistry who want to take full advantage of current solid-phase synthesis techniques.

A unique, integrated look at solid-phase synthesis and advances in combinatorial chemistry and technologies The last decade has seen a rapid expansion in combinatorial technologies, a field where chemistry disciplines intersect with automation, statistics, and information science, as well as certain biological disciplines. Reflecting these multidisciplinary trends, this new work provides a comprehensive overview of the most important aspects of solid-phase synthesis (SPS), combinatorial chemistry, and related combinatorial technologies. It clearly demonstrates how SPS and combinatorial chemistry have extended their application from the pharmaceutical arena to new areas, including biotechnology, material sciences, catalysis, and agrochemical industries, and explores in detail strategies for planning, designing, preparing, and testing of combinatorial libraries in various disciplines. Designed to meet the needs of both experienced combinatorial chemists and newcomers to the field, Solid-Phase Synthesis and Combinatorial Technologies: Surveys the most recent developments in SPS and combinatorial chemistry Explains the entire process, from determining the need for a library to the details necessary for synthesis of the library Discusses choice of format, size, and the rationale behind the design of each synthetic step Surveys the analytical techniques and the purification methods used to characterize and purify combinatorial libraries Employs a large number of examples to illustrate important concepts Includes problems geared toward applying acquired knowledge and designing the steps to SPS/library synthesis Describes the quality control and activity screening of combinatorial libraries for various applications Features a detailed bibliography of more than 1,700 relevant sources

Integrates solid-phase organic synthesis with palladium chemistry The Wiley Series on Solid-Phase Organic Syntheses keeps researchers current with major accomplishments in solid-phase organic synthesis, providing full experimental details. Following the validated, tested, and proven experimental procedures, readers can easily perform a broad range of complex syntheses needed for their own experiments and industrial applications. The series is conveniently organized into themed volumes according to the specific type of synthesis. This second volume in the series focuses on palladium chemistry in solid-phase synthesis, exploring palladium catalysts and reactions, procedures for preparation and utilization, ligands, and linker reactions. The first part of the volume offers a comprehensive overview of the field. Next, the chapters are organized into three parts: Part Two: Palladium-Mediated Solid-Phase Organic Syntheses Part Three: Immobilized Catalysts and Ligands Part Four: Palladium-Mediated Multifunctional Cleavage Each chapter is written by one or more leading international experts in palladium chemistry. Their contributions reflect a thorough examination and review of the current literature as well as their own first-hand laboratory experience. References at the end of each chapter serve as a gateway to the field's literature. The introduction of palladium-mediated, cross-coupling reactions more than thirty years ago revolutionized the science of carbon-carbon bond formation. It has now become a cornerstone of today's synthetic organic chemistry laboratory. With this volume, researchers in organic and medicinal chemistry have access to a single resource that explains the fundamentals of palladium chemistry in solid-phase synthesis and sets forth clear, step-by-step instructions for conducting their own syntheses.

The second volume in a series, Organic Synthesis: State of the Art 2005-2007 will provide you with a convenient, compact summary of the state of the art of organic synthesis. This reference guide will quickly lead you to the most important recent developments like how scientists can now prepare ketones by directly combining aldehydes with terminal alkenes. Inside, you will find detailed analysis of more than twenty total syntheses, including the Davies Synthesis of (-)-Colombiasin A and (-)-Elisapterosin B, the Overman Synthesis of (-)-Sarain A, and the Sorensen Synthesis of (-)-Guanacastepene E.

One approach to organic synthesis is retrosynthetic analysis. With this approach a chemist will start with the structure of their target molecule and progressively cut bonds to create simpler molecules. Reversing this process gives a synthetic route to the target molecule from simpler starting materials. This “disconnection” approach to synthesis is now a fundamental part of every organic synthesis course. Organic Synthesis: The Disconnection Approach, 2nd Edition introduces this important technique, to help students to design their own organic syntheses. There are forty chapters: those on the synthesis of given types of molecules alternate with strategy chapters in which the methods just learnt are placed in a wider context. The synthesis chapters cover many ways of making each type of molecule starting with simple aromatic and aliphatic compounds with one functional group and progressing to molecules with many functional groups. The strategy chapters cover questions of selectivity, protection, stereochemistry, and develop more advanced thinking via reagents specifically designed for difficult problems. Examples are drawn from pharmaceuticals, agrochemicals, natural products, pheromones, perfumery and flavouring compounds, dyestuffs, monomers, and intermediates used in more advanced synthetic work. Reasons for wishing to synthesise each compound are given. This second edition has been fully revised and updated with a modern look. Recent examples and techniques are included and illustrated additional material has been added to take the student to the level required by the sequel, “Organic Synthesis: Strategy and Control”. Several chapters contain extensive new material based on courses that the authors give to chemists in the pharmaceutical industry. Organic Synthesis: The Disconnection Approach, 2nd edition provides a full course in retrosynthetic analysis for chemistry and biochemistry students and a refresher for organic chemists working in industry and academia.

Organic Synthesis: Strategy and Control is the long-awaited sequel to Stuart Warren’s bestseller Organic Synthesis: The Disconnection Approach, which looked at the planning behind the synthesis of compounds. This unique book now provides a comprehensive, practical account of the key concepts involved in synthesising compounds and focuses on putting the planning into practice. The two themes of the book are strategy and control: solving problems either by finding an alternative strategy or by controlling any established strategy to make it work. The book is divided into five sections that deal with selectivity, carbon-carbon single bonds, carbon-carbon double bonds, stereochemistry and functional group strategy. A comprehensive, practical account of the key concepts involved in synthesising compounds Takes a mechanistic approach, which explains reactions and gives guidelines on how reactions might behave in different situations Focuses on reactions that really work rather than those with limited application Contains extensive, up-to-date references in each chapter Students and professional chemists familiar with Organic Synthesis: The Disconnection Approach will enjoy the leap into a book designed for chemists at the coalface of organic synthesis.

The first in a new series, this book provides chemists an effective, much-needed way to stay abreast of recent developments in organic synthesis. The 103 articles review the leading synthetic procedures developed from 2003 – 2005, discussing their significance and their applications. More than 100 reactions are covered, including Heterocycle Construction by Grubbs Metathesis, Enantioselective C-C Bond Construction, and Organic Reactions in Ionic Liquids.

This unusual collection of 49 essays gives an overview of the trends and accomplishments of synthetic organic chemistry in recent years. Unique in its approach, it deals with almost every aspect of modern synthesis. The first part of the book describes methods and reagents, with particular emphasis on rapidly developing organometallic and biooriented procedures. In the second part, these tools are applied to the syntheses of interesting target compounds and natural compounds with remarkable physiological properties. Mechanistic discussions and retrosynthetic analyses are included. More than 1000 up-to-date references help the reader to pursue the topics highlighted here. This book gives both the active researcher and the advanced student insight into the competitive atmosphere, creativity, and resourcefulness so characteristic of organic synthesis today.

Template-controlled reactions allow the synthesis of complex molecules which would hardly be achievable through classical methods. This handbook offers authoratative information on how noncovalent and covalent templates can be effectively applied to control reaction rates as well as regio- and stereoselectivity. From the concepts of template control such as molecular imprinting, self-replication, and reversible tether-directed remote functionalization, the reader is led to template-based ring-closing reactions, oligomerizations, and multiple functionalizations and their application in the synthesis of supramolecular scaffolds and natural products. The editors and authors (J. F. Stoddart, G. Wulf, D. Lynn, R. Breslow. F. Diederich, just to name a few ) , all internationally recognized experts in their area, succeeded in presenting the manifold aspects of template-controlled synthesis in a didactic way, making this methodology accessible to a broad readership of organic synthetic chemists. Well-selected, reliable key experimental protocols and an up-to-date reference list underline the practical approach of this valuable handbook. Being the first book of its kind, it will serve as a pacemaker and stimulate future research.