This clear and concise text is concerned with the reactions used in stereoselective organic synthesis. These are important types of reactions which can be used for the selective preparation of new organic compounds with a defined and predictable three dimensional architecture. This informative text will be an invaluable study aid for all undergraduate chemistry students. Undergraduates in related subjects studying chemistry to second year level or higher will also find this book useful.
Stereochemistry and Organic Reactions: Conformation, Configuration, Stereoelectronic Effects and Asymmetric Synthesis provides coverage on the stereochemistry of reactions of all mechanistic types, ranging from ionic, pericyclic and transition metal-catalyzed to radical and photochemical. Chapters cover acyclic molecules, cyclic molecules, the stereochemistry of organic reactions, the perturbation molecular orbital theory for the origin of stereoelectronic effects, and an introduction to the principles of stereoselectivity and hierarchical levels of asymmetric synthesis. Each chapter includes problems that reinforce main themes, making it valuable to students, teachers and researchers working in organic, biological and medicinal chemistry, as well as biologists, pharmacologists, polymer chemists and chemists. - Presents a holistic and unified approach to stereochemical understanding and predictions, covering reactions of all mechanistic classes - Includes two background chapters on perturbation theory and stereoselective principles, along with asymmetric designs - Features novel rules and mnemonics to delineate product stereochemistry - Includes up-to-date coverage with over 1300 selective references
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.
Introduces a new classification for stereoselective reactions based on the number of chiral centres contained in the starting material and the product. Based on stereochemical terms, this classification enables users to apply methods for the synthesis of target molecules.
Synthetically useful organic reactions or reagents are often referred to by the name of the discoverer(s) or developer(s). Older name reactions are described in text books, but more recently developed synthetically useful reactions that may have been associated occasionally with a name are not always well known. For neither of the above are experimental procedures or references easy to find. In this monograph approximately 500 name reactions are included, of which over 200 represent newer name reactions and modern reagents. Each of these reactions are extremely useful for the contemporary organic chemistry researcher in industry or academic institutions. This book provides the information in an easily accessible form. In addition to seminal references and reviews, one or more examples for each name reaction are provided and a complete typical experimental procedure is included, to enable the student or researcher to immediately evaluate reaction conditions. Besides an alphabetical listing of reactions and reagents, cross references permit the organic practitioner to find those name reactions or reagents that enable specific transformations, such as, conversion of amines to nitriles, stereoselective reduction, fluoroalkylation, phenol alkynylation, asymmetric syntheses, allylic alkylation, nucleoside synthesis, cyclopentanation, hydrozirconation, to name a few. Emphasis has been placed on stereoselective and regioselective transformations as well as on enantioselective processes. The listing of reactions and reagents is supported by four indexes.
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.
This work describes the essential aspects of enantioselective catalysis, with chapters organised by concept rather than by reaction type. Each concept is supported by examples to give the reader broad exposure to a wide range of catalysts, reactions and reaction mechanisms.
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
This book is an account for students of how the three-dimensional shapes of molecules influence their chemical and physical properties. It begins with the structures of molecules and then describes how such structures can be changed.
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. The aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions.
