The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal.
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.
Presents in a logical, readable manner the synthetic utility of amino acids for the generation of chiral agents, intermediates, and final products by means of asymmetric synthesis. In the past 20 years asymmetric synthesis has forged to the forefront of organic chemistry. This book provides extensive schemes and reactions containing over 1900 structures to illustrate the varied assortment of chiral intermediates that can be generated from amino acids and their derivatives. Focuses on the alpha[l.c. Greek letter]-amino acids and second-generation intermediates that can be derived therefrom which are of general interest to organic chemists, in either the industrial or the academic environment. Special attention has been paid to the asymmetric synthesis of key pharmaceutical agents, agrochemicals, and a host of natural products including alkoloids, terpenoids, carbohydrates, and insect pheromones. Includes extensive and up-to-date references.
Derived from the renowned, Encyclopedia of Reagents for Organic Synthesis (EROS), the related editors have created a new handbook which focuses on chiral reagents used in asymmetric synthesis and is designed for the chemist at the bench. This new handbook follows the same format as the Encyclopedia, including an introduction and an alphabetical arrangement of the reagents. As chiral reagents are the key for the successful asymmetric synthesis, choosing the right reagents is essential, in this handy reference the editors give details on how to prepare, store and use the reagents as well as providing key reactions to demonstrate where reagents have been successfully used. Comprehensive information on 226 reagents Covers 64 reagents which were not included in EROS All information in one easy to use volume – at an affordable price All reagents included will be added to e-EROS – please visit the site where you can gain access to over 50,000 reactions and 3,800 of the most frequently consulted reagents. Visit: www.interscience.wiley.com/eros
In this first book to gather the information on this hot topic otherwise widely spread throughout the literature, experienced editors and top international authors cover everything the reader needs -- from the synthesis of chiral organosulfur compounds to applications and catalysis: * Asymmetric synthesis of chiral sulfinates and sulfoxides * Synthesis and use of chiral dithioacetal derivatives, ylids, chiral sulfoximines and sulfinamides * Use of chiral sulfoxides as ligands in catalysis * Asymmetric reactions of alpha-sulfenyl, alpha-sulfinyl and alpha-sulfonyl carbanions. As a result, readers will be able to improve their own performance in asymmetric synthesis.
Asymmetric synthesis remains a challenge to practicing scientistsas the need for enantiomerically pure or enriched compoundscontinues to increase. Over the last decade, a large amount ofliterature has been published in this field. Principles andApplications of Asymmetric Synthesis consolidates and evaluates themost useful methodologies into a one-volume resource for theconvenience of practicing scientists and students. Authored by internationally renowned scientists in the field, thisreliable reference covers more than 450 reactions and includesimportant stoichiometric as well as catalytic asymmetric reactions.The first chapter reviews the basic principles, commonnomenclature, and analytical methods, and the remainder of the bookis organized according to reaction type. The text examines suchtopics as: Carbon-carbon bond formations involving carbonyls, enamines,imines, and enolates Asymmetric C-O bond formations including epoxidation,dihydroxylation, and aminohydroxylation Asymmetric synthesis using the Diels-Alder reaction and othercyclizations Applications to the total synthesis of natural products Use of enzymes in asymmetric synthesis Practicing chemists in the pharmaceutical, fine chemical, andagricultural professions as well as graduate students will findthat Principles and Applications of Asymmetric Synthesis affordscomprehensive and current coverage.
Axially Chiral Compounds Explore this comprehensive and current volume summarizing the characteristics, synthesis, and applications of axial chirality Appearing widely in natural products, biologically active molecules, asymmetric chemistry, and material science, axially chiral motifs constitute the core backbones of the majority of chiral ligands and organocatalysts in asymmetric catalysis. In a new work of particular relevance to synthetic chemists, Axially Chiral Compounds: Asymmetric Synthesis and Applications delivers a clearly structured and authoritative volume covering the classification, characteristics, synthesis, and applications of axial chirality. A must read for every synthetic chemist practicing today, the book follows the development history, research status, and applications of axial chirality. An introductory chapter familiarizes the reader with foundational material before the distinguished authors describe the different classes and the synthesis of axial chiral compounds used in asymmetric synthesis. The book concludes with a focus on the applications of chiral ligands, chiral catalysts, and materials. Readers will also benefit from the inclusion of: A thorough introduction to asymmetric synthesis, including biaryls atropisomers, heterobiaryls atropisomers, and non-biaryls atropisomers Explorations of chiral allene, spiro skeletons, and natural products Practical discussions of asymmetric transformation, chiral ligands, and chiral catalysts An examination of miscellaneous applications of axially chiral compounds Perfect for organic chemists, chemists working with or on organometallics, catalytic chemists, and materials scientists, Axially Chiral Compounds: Asymmetric Synthesis and Applications will also earn a place in the libraries of natural products chemists who seek a one-stop reference for compounds exhibiting axial chirality.
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
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.
Although many books exist on the subject of chiral chemistry, they only briefly cover chiral synthesis and analysis as a minor part of a larger work, to date there are none that pull together the background information and latest advances in one comprehensive reference work. Comprehensive Chirality provides a complete overview of the field, and includes chiral research relevant to synthesis, analytic chemistry, catalysis, and pharmaceuticals. The individual chapters in each of the 9 volumes provide an in depth review and collection of references on definition, technology, applications and a guide/links to the related literature. Whether in an Academic or Corporate setting, these chapters will form an invaluable resource for advanced students/researchers new to an area and those who need further background or answers to a particular problem, particularly in the development of drugs. Chirality research today is a central theme in chemistry and biology and is growing in importance across a number of disciplinary boundaries. These studies do not always share a unique identifying factor or subject themselves to clear and concise definitions. This work unites the different areas of research and allows anyone working or researching in chiral chemistry to navigate through the most essential concepts with ease, saving them time and vastly improving their understanding. The field of chirality counts several journals that are directly and indirectly concerned with the field. There is no reference work that encompasses the entire field and unites the different areas of research through deep foundational reviews. Comprehensive Chirality fills this vacuum, and can be considered the definitive work. It will help users apply context to the diverse journal literature offering and aid them in identifying areas for further research and/or for solving problems. Chief Editors, Hisashi Yamamoto (University of Chicago) and Erick Carreira (ETH Zürich) have assembled an impressive, world-class team of Volume Editors and Contributing Authors. Each chapter has been painstakingly reviewed and checked for consistent high quality. The result is an authoritative overview which ties the literature together and provides the user with a reliable background information and citation resource.
