Author
Dr. Hélène Pellissier
Aix Marseille Université
iSm2, UMR 7313, Case 561
Avenue Esc. Normandie‐Niemen
13397 Marseille
France
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Print ISBN: 978‐3‐527‐34619‐6
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The importance of chiral molecules in medicine has made asymmetric catalysis the most challenging field of modern organic chemistry [1]. Indeed, the use of chiral drugs in an enantiopure form is now a standard requirement for virtually every new chemical entity, and the development of new synthetic methods to obtain enantiopure compounds has become a key goal for pharmaceutical companies. Asymmetric synthesis constitutes one of the main strategies to achieve chiral compounds. Especially, asymmetric metal catalysis has been the subject of intense research in the past few decades to become a powerful tool to perform highly enantioselective transformations [2].
Another challenging goal in synthetic chemistry is the discovery of efficient routes for single‐step elaboration of relevant products from simple and readily available building blocks. This has become possible with the development of domino reactions [3]. The concept of domino reaction was introduced by Tietze in 1993 as a reaction that involves two or more bond‐forming transformations, taking place under the same reaction conditions, without adding additional reagents and catalysts, and in which the subsequent reactions result as a consequence of the functionality formed by bond formation or fragmentation in the previous step [4]. Ever since, an explosive number of these fascinating one‐pot reactions have been developed, allowing easily building complex chiral molecular architectures from simple materials to be achieved in one step, with economic advantages, such as avoiding costly protecting groups and time‐consuming purification procedures after each step. The more steps a domino reaction includes the greater is the probability to convert simple substrates into complex products. In addition to being economic, another advantage of these one‐pot reactions deals with the benefit on the environment and natural resources, since they allow reducing the waste produced compared to normal multistep procedures and minimize the amount of chemicals required for the preparation of products. Moreover, most of domino processes provide high stereocontrol and good yields. Actually, the immense development of enantioselective metal‐catalyzed domino reactions is a consequence of the considerable impact of the advent of asymmetric transition‐metal catalysis. The wide variety of asymmetric domino processes well reflects that of the metal employed to promote them. Among metals, the use of metals of high abundance, low cost, and toxicity, such as copper, cobalt, iron, magnesium, nickel, titanium, zinc, or zirconium, is in line with the new concept of green chemistry.
This book collects the major progress in the field of enantioselective one‐, two‐, and multicomponent domino reactions promoted by chiral metal catalysts, covering the literature since the beginning of 2006. It illustrates how enantioselective metal‐catalyzed processes constitute outstanding tools for the development of a wide variety of fascinating one‐pot asymmetric domino reactions, allowing a number of complex important products to be easily generated from simple materials in a single step. It strictly follows the definition of domino reactions by Tietze as single‐, two‐, as well as multicomponent transformations, excluding reactions in which the addition of the components is carried out sequentially or those requiring adjustment of the reaction conditions throughout the process.
The book is divided into twelve chapters, dealing successively with enantioselective copper‐, palladium‐, rhodium‐, scandium‐, silver‐, nickel‐, gold‐, magnesium‐, cobalt‐, zinc‐, yttrium and ytterbium‐, and other metal‐catalyzed domino reactions. Most of the chapters are divided into two parts dealing successively with one‐ and two‐component domino reactions, and three‐component processes. Each part is subdivided according to the nature of domino reactions. Each chapter of the book includes selected applications of synthetic methodologies to prepare natural and biologically active products.
The author hopes that this book will provide an insight into the present stage of asymmetric domino reactions promoted by chiral metal catalysts and stimulate the design of novel asymmetric domino reactions and their use in the synthesis of natural products, pharmaceuticals, agrochemicals, and materials not only in academic institutions but also in industry.
Hélène Pellissier is currently researcher at the National Center for Scientific Research (CNRS) at Aix‐Marseille Université (France). She carried out her PhD under the supervision of Dr. G. Gil in Marseille in 1987. After a postdoctoral period in Professor K.P.C. Vollhardt's group at the University of California, Berkeley, she joined the group of Professor M. Santelli in Marseille in 1992, where she developed novel very short total syntheses of unnatural steroids starting from 1,3‐butadiene and benzocyclobutenes. She is the author of 120 papers including reviews in international journals, 10 books, and 10 book chapters.