CRC Handbook of Optical Resolutions Via Diastereomeric Salt Formation

Addresses this important organic chemical process. Provides fast, one-stop access to a wealth of information, including all of the available data on 100 resolving agents, a list of 500 optically active compounds available in bulk, and data on more than 3,500 resolutions.

Research on optically active compounds is expanding both in academia and industry. Enantiopure forms of organic substances are increasingly important in a range of fields, such as pharmaceutical, agricultural, nonlinear optics and liquid crystal materials. It is known that living systems respond stereoselectively to any chiral substance introduced and that the desired effect of a chiral drug is associated with one of its enantiomer, so that it rational to apply only the enantiopure form. The new CRC handbook, Optical Resolution via Diastereomeric Salt Formation, offers a comprehensive survey on the most widely used method of obtaining pure enantiomers. Resolution of a racemate can be accomplished by two basically different methods: 1- formation of diastereometic derivatives by reacting the racemate with a chiral compound (the resolving agent), followed by separation of the products; and 2- by chromatography on a chiral stationary phase. The former is based on the principle when the pair of enantiomers, being the mirror image of each other and therefore having (apart from optical rotation) exactly identical physicochemical properties, is transformed without establishing a chemical bond with one, preferably pure enantiomer of the resolving agent to a pair of non-mirror-image derivatives (salts or complexes), i.e. diastereomers, which owing to their different scalar properties can be separated by conventional methods such as crystallization, distillation, extraction, sublimation, chromatography. The latter is an elegant and efficient method useful for analytical purposes and to separate small quantities of a racemate, but its use is very restricted in large-scale production. First discovered about 150 years ago by Louis Pasteur the number of resolutions accomplished since using this method now total about 10, 000. According to the Introduction there is no precedent for such a handbook, mostly because resolution methods involve a significant amount of know-how knowledge, best transferred by personal contacts. Thereby the aim was to present authorsÆ extensive experience covering both the theoretical aspects and practical examples. In the Foreword by Professor Kazuhiko Saigo the need and distinctions of the CRC Handbook are stressed. In one volume is contained a wealth of information on all aspects of the optical resolution of racemates by diastereomeric salt formation including principles of resolvability, mechanisms and kinetics, very valuable lists of commonly used resolving agents and of optically active commercially produced agents along with their suppliers, correlations between the resolvability and the structures of a racemate and a resolving agent, definite methods for the selection of a suitable resolving agent for a given racemate, explanations on the optimization of parameters for crystallization and modified methods with examples for optical resolution, and summaries of 4000 resolutions by diastereomeric salt formations, which are invaluable in resolving of an unknown racemate. The handbook consists of eight chapters and three data condensed appendixes (about 490 pages out of total 690). Following a brief Introduction (Chapter 1) and basic concepts and nomenclature of stereochemistry (Chapter 2), the resolution method by fractional crystallization, almost exclusively applied technique, is reviewed in Chapter 3. An extensive list of references sources (149) is given. Next, chapter 4 deals with resolving agents providing all available data for the most frequently used acidic and basic resolving agents (50 of each). The guidance to the selection of the resolving agent is offered in Chapter 5 and the way experiments must be performed in Chapter 6. Alternative (to fractional crystallization) techniques such as distillation, extraction, supercritical extraction, sublimation and mechanical separation of diastereomeric salt mixtures are summarized in Chapter 7. The last Chapter 8 presents experimental details of procedures for 50 resolutions some yet unpublished or in patents elaborated for industrial application. The following two Appendixes offer a large amount of data. Appendix 1 (184 pages) is a database for approximately 4000 resolutions, which allows compare the structures of racemates and resolving agents and collected in order to facilitate the selection of the best agent. A data sample box is illustrated. Appendix 2 (46 pages) is a collection of nearly 500 optically active compounds produced on a commercial scale eligible as resolving agents and potential sources. Given here are the names of companies and the Internet addresses (excluding well known major companies supplying fine chemicals due to easy access to their catalogs and product information on the Internet) and alphabetically ordered lists of optically active bases and acids produced on an industrial scale. The discussion is concluded by Appendix 3, "Chiral Selective Chromatographic Analysis," a short practical introduction to chromatographic methods amenable to the determination of optical purity. As indicated by the authors this topic is covered due to the importance to know both techniques of preparing an optically active product and methods of checking its purity.The handbook is well organized to facilitate fast access to the information and data. Each chapter starts with an introduction to stress the basic concepts and provide explanatory notes and concludes by a list of suggested readings. Many diagrams, tables and equations are scattered throughout the text. Basically, the source is intended to serve as an easily readable reference companion.It is an authoritative information resource based on the contributions of five Ph.D. scientists and the Editor, David Kozma. The authors in majority work at the Department of Organic Chemical Technology Budapest University of Technology and Economics, Hungary. David Kozma is the co-author of a numbers of patents and 45 scientific papers published in a range of journals, i.e. Chirality, Synthetic Communications, Journal of Thermal Analysis and Calorimetry, TetrahedronÆs series, Journal of Chemical Research, Enantiomer, Journal of the Chemical Society. It is claimed that the book contains information obtained from authentic and highly regarded sources and all sources are indicated.The handbook will be useful for researchers, engineers, and graduates, who are interested in the studies of optical resolution of racemates by diasatereomeric salt formation. For a prize of $139.95 it is affordable for many research libraries, laboratories and personal collections. "Owing to the still rather obscure mechanism of resolution, separation of new racemate remains a challenge. It is the authorsÆ hope that this handbook will help readers to be able to answer this challenge-ever more often successfully."