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Authored by one of the world?s leading synthetic chemists in the field, this reference presents modern enolate chemistry with an emphasis on metal O-enolates in asymmetric synthesis. While great care is taken to cover novel, successful concepts, such classical methods as the famous Evans enolates are equally highlighted. Throughout the book representative reaction procedures are presented, thus helping readers to find the best solution for their own synthetic problem. Of high interest to synthetic chemists in academia, as well as the pharmaceuticals, agrochemicals and fine chemicals industries.
Aldol Reactions provides a comprehensive up-to-date overview of aldol reactions including application of different metal enolates; catalytic aldol additions catalyzed by different Lewis acids and Lewis bases; enantioselective direct aldol additions; antibodies and enzyme catalyzed aldol additions and the recent aggressive development of organocatalyzed aldol additions. The power of each method is demonstrated by several applications in total synthesis of natural products. The pros and cons of these methodologies with regard to stereoselectivity, regioselectivity and application in total synthesis of natural products are discussed. Great importance is set to the diverse possibilities of the manual of aldol reaction to install required configurations in complicated natural product synthesis.
At long last, the complete spectrum of the aldol reaction is presented here in this two-volume handbook. Top authors guarantee contributions of the highest quality, beginning with fundamentals and then moving on to enolates and catalytic aldol reactions, including the Mukaiyama Reaction. Further sections are devoted to enzymatic aldol reactions in synthesis as well as such related reactions as the Henry, Ene and Aldol-Tishchenko reactions. The wealth of information contained here allows a comprehensive overview of this important topic in organic chemistry, removing the need for the hitherto time-consuming research among the widely dispersed literature. With a foreword by Professor D. A. Evans.
Metal Enolates form a class of compounds that have recently received much study because of their part in the important C-C-bond forming aldol reaction. Focusing on this important class of compounds in organic synthesis, The Chemistry of Metal Enolates features contributions on all aspects of Metal Enolate chemistry from the world?s leading experts. Delivering the exceptional quality that?s expected from the Patai Series, this text is essential reading for organic chemists.
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 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 collection of the six contributions of the 7th International Seminar on Modern Synthetic Methods, written by leading experts in their fields, gives an overview on the state of the art, trends, and new accomplishments in solvent effects on chemical transformations, in reactions on surfaces, in the synthesis of oligosaccharides and nucleid acid analogues, and in antibody catalyis. This volume is an invaluable companion to both the active research chemists and the advanced students, fascinated by the world of biologically important compounds and by the creativity in synthetic techniques directed towards their preparation.
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
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.