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Selectivity is an increasingly 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 aim is to illustrate 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 aims to provide a solid introduction to this subject, focusing on the key areas and applications.
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.
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.
Organic Synthesis, Fourth Edition, provides a reaction-based approach to this important branch of organic chemistry. Updated and accessible, this eagerly-awaited revision offers a comprehensive foundation for graduate students coming from disparate backgrounds and knowledge levels, to provide them with critical working knowledge of basic reactions, stereochemistry and conformational principles. This reliable resource uniquely incorporates molecular modeling content, problems, and visualizations, and includes reaction examples and homework problems drawn from the latest in the current literature. In the Fourth Edition, the organization of the book has been improved to better serve students and professors and accommodate important updates in the field. The first chapter reviews basic retrosynthesis, conformations and stereochemistry. The next three chapters provide an introduction to and a review of functional group exchange reactions; these are followed by chapters reviewing protecting groups, oxidation and reduction reactions and reagents, hydroboration, selectivity in reactions. A separate chapter discusses strategies of organic synthesis, and he book then delves deeper in teaching the reactions required to actually complete a synthesis. Carbon-carbon bond formation reactions using both nucleophilic carbon reactions are presented, and then electrophilic carbon reactions, followed by pericyclic reactions and radical and carbene reactions. The important organometallic reactions have been consolidated into a single chapter. Finally, the chapter on combinatorial chemistry has been removed from the strategies chapter and placed in a separate chapter, along with valuable and forward-looking content on green organic chemistry, process chemistry and continuous flow chemistry. Throughout the text, Organic Synthesis, Fourth Edition utilizes Spartan-generated molecular models, class tested content, and useful pedagogical features to aid student study and retention, including Chapter Review Questions, and Homework Problems. A full Solutions Manual is also available online for qualified instructors, to support teaching. - Winner, 2018 Textbook Excellence Award (Texty) from the Textbook and Academic Authors Association - Fully revised and updated throughout, and organized into 19 chapters for a more cogent and versatile presentation of concepts - Includes reaction examples taken from literature research reported between 2010-2015 - Features new full-color art and new chapter content on process chemistry and green organic chemistry - Offers valuable study and teaching tools, including Chapter Review Questions and Homework Problems for students; Solutions Manual for qualified course instructors
Bringing together examples that until now were often hidden and widely spread throughout the original literature, this textbook shows how to use the correct reagents, conditions or reaction sequences to have access to all possible stereoisomers when beginning synthesis with only a single starting material. Adopting a didactic approach, the authors have chosen general and simple examples throughout the book so that these reactions can be transferred easily to other reaction types. While of major interest to master and PhD students alike, this book is also a source of valuable information for organic chemists in both academia and industry. Additional material for lectures at www.wiley-vch.de/textbooks
Volume 8.
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.
Organic Synthesis Using Biocatalysis provides a concise background on the application of biocatalysis for the synthesis of organic compounds, including the important biocatalytic reactions and application of biocatalysis for the synthesis of organic compounds in pharmaceutical and non-pharmaceutical areas. The book provides recipes for carrying out various biocatalytic reactions, helping both newcomers and non-experts use these methodologies. It is written by experts in their fields, and provides both a current status and future prospects of biocatalysis in the synthesis of organic molecules. - Provides a concise background of the application of biocatalysis for the synthesis of organic compounds - Expert contributors present recipes for carrying out biocatalytic reactions, including subject worthy discussions on biocatalysis in organic synthesis, biocatalysis for selective organic transformation, enzymes as catalysis for organic synthesis, biocatalysis in Industry, including pharmaceuticals, and more - Contains detailed, separate chapters that describe the application of biocatalysis
The view of organic synthesis as "a concentrated expression of predictive ability and creative capacity" was advocated in the early 1950s. A concise and readable account of the role of synthesis in modern science, Organic Synthesis: The Science Behind the Art presents the general ideology of pursuits in the area of organic synthesis, and examines the methodologies that have evolved in the search for solutions to synthetic problems. This unique book details outstanding achievements of modern organic synthesis, not only for their scientific merits, but also for the aesthetic appeal of the target molecules chosen and the intrinsic beauty of the solutions to the problems posed. By judicious selection of data covering the main areas of synthetic explorations, this book serves to illustrate both the evolution of well-known approaches as well as recently emerged trends most likely to determine the future development of organic synthesis. Special attention is given to the consideration of principles of molecular design in promising and challenging areas of current research. Primarily aimed at advanced undergraduate and graduate students, Organic Synthesis: The Science Behind the Art will also be of interest to teachers, researchers and anyone requiring an introduction to the problems of organic synthesis.
The stepping-stone text for students with a preliminary knowledge of organic chemistry looking to move into organic synthesis research and graduate-level coursework Organic synthesis is an advanced but important field of organic chemistry, however resources for advanced undergraduates and graduate students moving from introductory organic chemistry courses to organic synthesis research are scarce. Introduction to Strategies for Organic Synthesis is designed to fill this void, teaching practical skills for making logical retrosynthetic disconnections, while reviewing basic organic transformations, reactions, and reactivities. Divided into seven parts that include sections on Retrosynthesis and Protective Groups; Overview of Organic Transformations; Synthesis of Monofunctional Target Molecules; Synthesis of Target Molecules with Two Functional Groups; Synthesis of Aromatic Target Molecules; Synthesis of Compounds Containing Rings; and Predicting and Controlling Stereochemistry, the book covers everything students need to successfully perform retrosynthetic analyses of target molecule synthesis. Starting with a review of functional group transformations, reagents, and reaction mechanisms, the book demonstrates how to plan a synthesis, explaining functional group analysis and strategic disconnections. Incorporating a review of the organic reactions covered, it also demonstrates each reaction from a synthetic chemist's point of view, to provide students with a clearer understanding of how retrosynthetic disconnections are made. Including detailed solutions to over 300 problems, worked-through examples and end-of-chapter comprehension problems, Introduction to Strategies for Organic Synthesis serves as a stepping stone for students with an introductory knowledge of organic chemistry looking to progress to more advanced synthetic concepts and methodologies.