1
NATURE CHEMISTRY | VOL 1 | SEPTEMBER 2009 | www.nature.com/naturechemistry 423 books & arts T his 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. e 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. ere 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. e symmetry, shape and dynamics of catalysts are discussed in depth and much insight is provided by the high-quality drawings. ese 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. ere 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. e one thing that I miss most here is much discussion of related biocatalytic processes. roughout the chapters a number of examples of enzyme- catalysed reactions are given, but the main focus is clearly on ‘man-made’ catalysts. is is also true for the discussions of terms and processes. On the other hand, the combined treatment of metal and organocatalysis is admirable. e 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. e 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’. is 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. REVIEWED BY ADRIAAN J. MINNAARD Adriaan J. Minnaard is Professor in Bio-organic Chemistry at the University of Groningen, the Netherlands. Comprehending catalysis Fundamentals of Asymmetric Catalysis by Patrick J. Walsh and Marisa C. Kozlowski UNIVERSITY SCIENCE BOOKS: 2009. 750PP. £52.99 ON OUR BOOKSHELF Catalysis for Sustainable Energy Production Edited by Pierluigi Barbaro and Claudio Bianchini WILEY-VCH: 2009. 452PP. £130 The development of new and efficient catalysts will have a significant impact on achieving the environmental goals that are currently a major focus of political discussion. Covering subjects including fuel cells and removal of pollutants, this monograph provides a invaluable starting point for anyone interested in the role of chemistry in sustainability. Forensic Chemistry of Substance Misuse: A Guide to Drug Control by Leslie A. King RSC: 2009. 270PP. £49.95 Building on a 2003 publication by the same author, this book gives a chemical insight into the legal controls of drugs from the UK, US and New Zealand perspectives. Chapters cover, for instance, a recent history of the drug-classification debate, with technical material included in some 20 appendices. © 2009 Macmillan Publishers Limited. All rights reserved

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NATURE CHEMISTRY | VOL 1 | SEPTEMBER 2009 | www.nature.com/naturechemistry 423

books & arts

This text is organized diff erently compared with most other books in the fi eld: 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 eff ects 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.

Th e 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. Th ere 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. Th e symmetry, shape and dynamics of catalysts are discussed in depth and much insight is provided by the high-quality drawings.

Th ese chapters are followed by a discussion on the intriguing topic of non-classical catalyst substrate interactions Specifi c attention is paid to C–H. . .π and C–H. . .O interactions that are occasionally observed, and the eff ects 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.

Th ere 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. Th e one thing that I miss most here is much discussion of related biocatalytic processes. Th roughout the chapters a number of examples of enzyme-catalysed reactions are given, but the main focus is clearly on ‘man-made’ catalysts. Th is is also true for the discussions of terms and processes. On the other hand, the combined treatment of metal and organocatalysis is admirable. Th e 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 eff ects, autocatalysis, and autoinduction’ will be extremely interesting.

Th e fi nal four chapters discuss the application of asymmetric catalysis. Numerous worked examples from across the entire fi eld 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 scientifi c 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’. Th is 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 fi eld. 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. ❐

REVIEWED BY ADRIAAN J. MINNAARD

Adriaan J. Minnaard is Professor in Bio-organic Chemistry at the University of Groningen, the Netherlands.

Comprehending catalysisFundamentals

of Asymmetric

Catalysis

by Patrick J. Walsh and

Marisa C. Kozlowski

UNIVERSITY SCIENCE

BOOKS: 2009. 750PP.

£52.99

ON

OU

R B

OO

KS

HE

LF

Catalysis for Sustainable Energy ProductionEdited by Pierluigi Barbaro and Claudio Bianchini

WILEY-VCH: 2009. 452PP. £130

The development of new and effi cient catalysts

will have a signifi cant impact on achieving the

environmental goals that are currently a major focus

of political discussion. Covering subjects including

fuel cells and removal of pollutants, this monograph

provides a invaluable starting point for anyone

interested in the role of chemistry in sustainability.

Forensic Chemistry of Substance Misuse: A Guide to Drug Controlby Leslie A. King

RSC: 2009. 270PP. £49.95

Building on a 2003 publication by the same author,

this book gives a chemical insight into the legal

controls of drugs from the UK, US and New Zealand

perspectives. Chapters cover, for instance, a recent

history of the drug-classifi cation debate, with

technical material included in some 20 appendices.

nchem_.339_SEP09.indd 423nchem_.339_SEP09.indd 423 11/8/09 14:46:0911/8/09 14:46:09

© 2009 Macmillan Publishers Limited. All rights reserved