Fundamentals of Asymmetric Catalysis

  • Patrick J. Walsh &
  • Marisa C. Kozlowski
UNIVERSITY SCIENCE BOOKS: 2009 750 pp. £52.99

This text is organized differently compared with most other books in the field: it is organized by sub-topic rather than by reaction type. It lures the reader into examining the fundamental concepts of the subject, with each backed up by the vast number of examples of reaction types.

Chapter 1 of Fundamentals covers 'Modes of asymmetric induction' which comprises the general concepts of catalysis, including the Curtin–Hammett Principle, temperature effects on enantioselectivity, and (dynamic) kinetic resolution. Such topics are immediately revealing for many researchers — especially those who use catalysts regularly but are not involved in the basic issues concerning the development of new ones.

The following two chapters examine the activation modes of catalytic asymmetric reactions and are split into two general groups. First those in which activation can be described by the action of a Lewis acid or Lewis base — both metal catalysis and organocatalysis are covered. There has been much recent progress in catalytic processes involving hydrogen bonds, chiral cations and anions and the third chapter is especially timely. Chapter 4 'Asymmetric induction in enantioselective catalysis' necessarily focuses on the ligands and catalysts. The symmetry, shape and dynamics of catalysts are discussed in depth and much insight is provided by the high-quality drawings.

These chapters are followed by a discussion on the intriguing topic of non-classical catalyst substrate interactions Specific attention is paid to C–H...π and C–H...O interactions that are occasionally observed, and the effects of which are probably more frequently encountered. In addition, the interaction of charges as seen, for example, in the well-known asymmetric phase transfer catalysis, is described.

Chapter 6, 'Chiral poisoning, chiral activation, and screening achiral ligands', is especially insightful, given the bewildering variety of methods to increase the enantioselectivity of a catalytic reaction.

There are many reviews and book chapters that discuss kinetic resolution, but the chapter covering this topic in Fundamentals is still very useful — all the more so because it pays ample attention to the more complicated variations on the theme. The one thing that I miss most here is much discussion of related biocatalytic processes. Throughout the chapters a number of examples of enzyme-catalysed reactions are given, but the main focus is clearly on 'man-made' catalysts. This is also true for the discussions of terms and processes. On the other hand, the combined treatment of metal and organocatalysis is admirable. The resolution theme continues in the next two chapters, which cover dynamic kinetic resolutions and dynamic kinetic asymmetric transformations. Given the importance of these processes, especially in industrial settings, these chapters are a must for researchers interested in the synthesis of compounds on a preparative scale.

Chapter 10 'Desymmetrization reactions' comprehensively describes the use of enantiotopic centres and so-called meso-tricks in asymmetric catalysis. For the stereochemist, including those working on topics like chirogenesis (the origin of homochirality), autocatalysis, symmetry-breaking, absolute asymmetric synthesis and the like, chapter 11 about 'Nonlinear effects, autocatalysis, and autoinduction' will be extremely interesting.

The final four chapters discuss the application of asymmetric catalysis. Numerous worked examples from across the entire field and the discussion of topics such as double diastereoselection, multistep asymmetric catalysis, supported chiral catalysts and the synthetic applications of asymmetric catalysis, make these a pleasure to read.

When I judge a scientific book, I start by looking at the index: I was not disappointed here — on the contrary! Next to a carefully composed index, the book contains a comprehensive appendix on 'Terms and enantioselective processes in asymmetric catalysis'. This appendix is carefully worked out and illustrated. I have no doubt that Fundamentals of Asymmetric Catalysis by Walsh and Kozlowski will become the reference work for researchers and teachers in the field. On the book shelf it will probably be placed between Stereochemistry of Organic Compounds by Eliel, Wilen and Mander and Comprehensive Asymmetric Catalysis by Jacobsen, Pfaltz and Yamamoto.

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