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Organic Synthesis: Strategy and Control by Paul Wyatt and Stuart Warren John Wiley and Sons Ltd.: Chichester, England, 2007. 918 pp; ISBN: 978-0471929635 (paper), $90; ISBN: 978-0471489405 (cloth), $190.
J. Chem. Educ. 2008.85:785. Downloaded from pubs.acs.org by 193.93.193.239 on 10/04/18. For personal use only.
reviewed by Richard Pagni
I suspect that when future historians of chemistry examine the six decades after the end of World War II, they will describe it as a golden age of organic synthesis. A great many reactions were discovered and characterized in this period. Mechanisms were elucidated for many of them and intelligent conjectures were made for the others. The use of transition metals in synthesis came to the fore. It became possible to link atoms in ways that previously had seemed inconceivable. Asymmetric versions of most of the new reactions were developed. New and better methods of separating compounds and resolving enantiomers were discovered. Organic photochemistry came into its own during this period, which led to reactions that have no counterpart in traditional organic chemistry. Stereoelectronic factors influencing the course of reactions were much better understood, both theoretically and experimentally. The retro-synthetic method of analysis was devised and refined. The role of the solvent in influencing the rate, stereochemistry, and regiochemistry of reactions became much better understood. High-powered, sophisticated quantum mechanical calculations became available and aided in all of the above tasks. As a result the synthesis of more and more complex natural products, pharmaceuticals, and unnatural products could be tackled in a rational and straightforward manner, provided that a chemist had a good grounding in the topics mentioned above. How may a student hope to master this complex, diverse, and sophisticated material? The student may begin by reading the current chemical literature regularly, although this will be frustrating when first attempted. The student may also take classes on these subjects, attend journal clubs and seminars, and read and study relevant books. It is in this latter area that I am happy to recommend Wyatt’s and Warren’s latest book, Organic Synthesis: Strategy and Control, as an excellent resource on organic synthesis. Because of the enormous breadth and complexity of the subject, being able to organize the material into coherent units as well as interconnecting them into a coherent whole is key to writing a successful book on organic synthesis. The authors, both British academic organic chemists, show this skill in abundance. They have clearly given considerable thought to ordering the vast amount of material they present. Because they obviously know the older and current literature well, they are adept at selecting just the appropriate synthesis at the right place in the book. They also cleverly show in several instances where a reaction sequence did not work, or did not work well, and then present another sequence that was found to be superior. In spite of all the chem-
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
istry we know, we can never be certain that a planned synthesis will be successful. There is still much to be discovered. I suspect that the only way you can appreciate the organizational skill of the authors is to examine the book on your own. I hope that I can mention a few of the book’s features that may help you decide whether you wish to examine it. The book is divided into five sections, roughly equal in length: selectivity; C–C single bonds; C–C double bonds; stereochemistry; and functional group strategy. Each section in turn is divided into from five to 12 chapters. The section on forming C–C single bonds, perhaps the most important task in organic synthesis, contains chapters on the ortho strategy for aromatic compounds, σ-complex of metals, controlling the Michael reaction, specific enol equivalents, extended enolates, allyl anions, homoenolates, and acyl anion equvalents. Consider further one chapter in this section, the one on homoenolates. Using well thought out examples, the authors show how to prepare the anionic transients and in turn how to use them in interesting synthetic applications, not all of which involve natural products or pharmaceuticals. Examples have been primarily from the recent literature, which a reader may consult for further details. The chapter on homoenolates, for example, has 45 references, with none published earlier than 1970. Mechanistic details feature prominently in the analyses of the syntheses in this and every other chapter. The authors rightly feel that a chemist cannot do good synthetic work without a sound understanding of reaction mechanisms. A novel feature of the book is that many of the syntheses have originated in industrial and pharmaceutical laboratories. The drawings, which must number in the tens of thousands in total and close to two hundred in the chapter on homoenolates, are beautifully drawn throughout. The narrative in each chapter is clear and lucid (an important characteristic in any textbook) and very concise (a necessary feature in a book that is already immensely long). I found very few errors in grammar, incorrectly drawn structures, incorrectly numbered structures, and other kinds of typographical problems. The authors have spent approximately ten years putting this excellent book together, and their hard work has paid off. Undergraduate and graduate students and professional chemists, both industrial and academic, will benefit greatly from reading it. I have always prided myself on my knowledge on current organic chemistry including synthesis, even though that is not my primary research interest. I confess that I have added many new reactions and techniques to my tool kit after having read this book. Supporting JCE Online Material
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Richard Pagni is in the Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600;
[email protected].
© Division of Chemical Education • www.JCE.DivCHED.org • Vol. 85 No. 6 June 2008 • Journal of Chemical Education
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