Book reviews

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Oligosaccharides: Their synthesis and biological roles

H. Osborn and T. Khan, Oxford University Press, 2000, pp. 112, price £80.95, ISBN 0-19-850260-5 Search PubMedOligosaccharides have for a long time been the central topic in carbohydrate chemistry. It is therefore essential that students entering research in modern carbohydrate chemistry be taught the essentials about oligosaccharide chemistry and biology. The present book tries to meet this demand and succeeds quite well.

Most textbook coverage of carbohydrate chemistry contains a large proportion of monosaccharide chemistry, which often makes the coverage quite voluminous and less suited for a short course in carbohydrates or as a text you expect graduate students to cover before starting their project. As monosaccharide chemistry is included in the standard organic chemistry books it is not really needed. Furthermore little carbohydrate biology is covered in most biochemistry or carbohydrate texts.

The book “Oligosaccharides. Their synthesis and biological roles” solves this problem. The basics of nomenclature and structure is given in a short introduction. Then a very valuable chapter on oligosaccharide biology in relation to medicine follows. This is perhaps the most important section. The rest of the book deals with synthesis of oligosaccharides: Synthesis of glycosyl donors, glycosyl acceptors, glycoside couplings and total synthesis examples. Finally a chapter describing enzymatic and solid phase oligosaccharide synthesis completes the book. The synthetic chapters describe some of the more colorful developments in the field over the last decade, and do not cover older methods to any great extent.

All in all the book is excellent for its purpose as an introduction to the beginning graduate student. It teaches the student the basics about oligosaccharide synthesis and biology in an easily understandable and entertaining way. I gave the book to a couple of my students, and they were very happy with it. The coverage is not deep, however, and there is little to gain for those knowledgeable in the field.

Mikael Bols
Aarhus University, Denmark

Catalytic Asymmetric Synthesis

Iwao Ojima, Wiley, New York, 2000, pp. xiv + 864, price £80.95, ISBN 0-471-29805-0 Search PubMedBack by popular demand! The first edition of Catalytic Asymmetric Synthesis was published in 1993 when its subject was a very exciting and rapidly developing research area. Since then the pace of development in the area has been so great and applications so many that catalytic asymmetric synthesis enters the 21st century as a mainstream chemical technology. As a consequence the first edition of this book now offers only an interesting historical perspective on the subject, and this second edition is extremely welcome.

The book is divided into 11 chapters each dealing with a different reaction type and each authored by experts in the area. The following list speaks for itself! Asymmetric hydrogenation (Noyori), asymmetric hydrosilylation and related reactions (Itoh), asymmetric isomerization of allylamines (Akutagawa), asymmetric carbometallations (Negishi), asymmetric addition and insertion reactions of catalytically generated metal carbenes (Doyle), asymmetric oxidations and related reactions (Sharpless, Katsuki, Kagan and Bolm), asymmetric carbonylations (Ojima), asymmetric carbon–carbon bond-forming reactions (Maruoka, Ito, Carreira, Mikami, Shibasaki, Trost, Hayashi and Overman), asymmetric amplification and autocatalysis (Soai), asymmetric phase-transfer reactions (O’Donnell) and asymmetric polymerization (Okamoto). The chapters on asymmetric carbometallations, asymmetric amplification and autocatalysis, and asymmetric polymerization are new to this edition and there has been significant expansion and development in the asymmetric carbon–carbon bond-forming reactions section so that this chapter now includes cycloaddition reactions, aldol reactions, ene reactions, Michael reactions, allylic alkylation reactions, cross-coupling reactions and Heck reactions.

The book has a fascinating appendix in which the chiral ligands mentioned in each chapter are summarized with appropriate references. Browsing through the 56 pages of this section provides a stunning reminder of the beauty, diversity and sheer numbers of chiral ligands now used in catalytic asymmetric synthesis.

This is a tremendous resource and an excellent read. I recommend immediate purchase – this may be the last time that catalytic asymmetric synthesis can be covered so comprehensively in one volume with contributions from so many pioneers of the field.

Susan E. Gibson
King's College, London, UK

Experimental Organic Chemistry

Daniel R. Palleros, John Wiley and Sons, 2000, pp. xxiv + 833, price £58.95, ISBN 0-471-28250-2 Search PubMedThe experience that a student has of organic chemistry in the laboratory can provide the motivation for understanding and learning the subject. A student who enjoys laboratory work is much more likely to become a proficient organic chemist. In writing this practical book, the author has tried to introduce experiments that relate to the student’s everyday experience of organic chemistry including its biological and medical applications.

The book is in three sections each containing a number of units. The first section is entitled ‘the basics’. This section starts with a unit on laboratory safety and continues with units on basic concepts and operations associated with the design of organic experiments and laboratory procedures. As well as a description of the physical chemical basis of various techniques, there are instructions on writing up and on searching the literature. The main body of the book is the second section, entitled ‘the experiments’. There are twenty six units. Each unit comprises several related experiments such as a preparation or isolation followed by a spectroscopic or gas chromatographic analysis. Each unit starts with a brief description of the underlying chemistry followed by the detailed experimental method. There are questions that a student might find helpful to answer before tackling the experiment and others that are better answered in the laboratory. There are margin notes on the potential hazards of particular steps and on the safe handling and disposal of chemicals. Some of the experiments involve micro and semi-micro scale methodology.

The first few units contain experiments to illustrate the basic techniques of organic chemistry such as recrystallization, extraction, distillation, gas chromatography, thin layer chromatography, column chromatography, HPLC, the measurement of refractive index and optical rotation. Subsequent units are devoted to the reactions of groups of compounds such as alcohols, alkyl halides, aldehydes, ketones and esters and to specific synthetic procedures such as electrophilic and nucleophilic aromatic substitution, the Diels–Alder reaction and oxidation and reduction. The final group of units in this second section cover more advanced topics such as multi-step syntheses, proteins, carbohydrates, nucleic acid bases, lipids, polymers and dyestuffs and some biotransformations.

The third section of the book contains units on the application of the major spectroscopic methods (UV, IR, NMR and MS) to organic chemistry. This section contains a description of the underlying theory, useful correlation tables and illustrative spectra together with some problems.

Although the book contains a number of well known experiments, there are many experiments that are novel and reflect aspects of biological organic chemistry. These include the isolation and characterization of natural products such as the constituents of essential oils and the preparation of biologically active compounds. There are some interesting experiments involving a biotransformation with a baker’s yeast.

The book is very well-illustrated with formulae, diagrams of apparatus and with spectra. The instructions are clearly written and the student is carefully guided through the operations necessary to successfully complete the experiment. The book is written for the American market and consequently some of the trivial names reflect this. However, the experiments are optimistic about the level of equipment to be found in an undergraduate laboratory. This is not just confined to the chromatographic and spectroscopic equipment but also to some of the more general laboratory equipment which would not normally be available outside a research laboratory. Very few of the units could be carried out by a laboratory class in their entirety here. This book will provide interesting reading for those responsible for the development of undergraduate practical classes. It contains a number of stimulating suggestions which could be adapted for use.

James R. Hanson*
University of Sussex, UK

Modern Amination Methods

Alfredo Ricci, Wiley-VCH, Wein heim, 2000, pp. xviii + 267, price £75, ISBN 3-527-29976-9 Search PubMedThe editor comments that this text is intended to provide an overview of several areas of research in which amination plays a key role, in particular, introducing new concepts recently developed for the formation of C–N bonds. The emphasis throughout is placed on asymmetric methodology (where appropriate) however, some important aspects of non-asymmetric applications are also included. One important point to note is that this text is not intended to be fully comprehensive and indeed some key areas such as hydroxy amination are not covered. Having read the text I feel that it would be well suited to advanced students of organic chemistry and professionals alike who have an interest in the synthesis of nitrogen containing target molecules be they natural products or potential therapeutic agents.

The book is divided into seven chapters each written by internationally recognised experts in their particular field. Each chapter includes full reference citations which significantly adds to the value of the text particularly for newcomers to the area. A detailed table of contents enables the reader to navigate through the text according to their own specific areas of interest. As one would expect from authors of this standing the quality of the schemes and figures is excellent throughout.

Chapter one deals with the synthesis of allyl amines by nucleophilic substitution of compounds possessing an allyl functionality (C–X cleavage) and direct allylic amination of simple alkenes (C–H cleavage). The chapter provides an overview of major developments in the area up to 1999. Reactions involving C–X cleavage are introduced in the context of non-asymmetric variants with a good level of mechanistic discussion followed by examples of asymmetric applications; however, the range of examples covered is perhaps not as extensive as it could be. Reactions involving C–H cleavage are less well developed, a fact that is highlighted by the limited number of enantioselective variants included here.

Chapter two covers the electrophilic amination of alkenes, the emphasis being largely placed on hydroboration of alkenes as a route to amination precursors. The direct amination of alkenes catalysed by transition metal complexes is also briefly mentioned. Background to the methodology presented here is given for non-asymmetric examples, however, the main focus of the chapter is on asymmetric methodology. The section on hydroboration can be roughly divided in two; starting with the use of chiral borane reagents and moving on to the application of transition metal catalysed hydroboration.

Chapter three introduces the topic of stereoselective electrophilic amination with sulfonyloxy carbamates and azodicarboxylates. Methods for the preparation and synthetic application of a wide range of electrophilic nitrogen sources are discussed in detail. In general the stereoselective methods discussed focus on the use of chiral auxiliaries attached to the nucleophile (principally enamines, enol ethers and enolates) although a brief discussion of chiral nitrogen sources and a catalytic asymmetric approach are also included.

Chapter four provides an introduction to the use of glycosylamines as chiral auxiliaries for use in the synthesis of chiral amino compounds. Properties of the auxiliaries and aspects of their mode of stereocontrol are briefly introduced. The main focus of the chapter is the application of this methodology to the synthesis of α- and β-amino acids, their use in multicomponent reactions such as the Ugi reaction and the synthesis of nitrogen heterocycles via cycloaddition reactions.

Chapter five describes the synthesis of transition metal nitride complexes in great detail. It is difficult to see how this chapter fits in with the rest of the text until you read Chapter six which, deals with the use of nitrido manganese complexes in nitrogen transfer reactions. The main focus of this chapter is the synthesis of chiral nitrido manganese complexes and their application in asymmetric aziridination of a range of olefins. The main limitation of the methodology described here is the requirement for stoicheiometric amounts of the nitrido complex, however, since this is a relatively new field catalytic variants will no doubt appear in the future. Disappointingly this chapter makes little mention of other aziridination methodologies covering copper catalysed reactions only very briefly.

Finally chapter seven deals with palladium catalysed amination of aryl halides and sulfonates. The discussion includes an overview of methodology development, synthetic information and pertinent mechanistic data for a range of amination reactions. The coverage of applications of this methodology is very extensive and gives the reader a good insight into its scope and limitations.

Overall the text does provide an overview of aspects of modern amination chemistry and gives a glimpse at where the future may lie in this key field of methodology development. If you are new to the area it will provide you with a good starting point from which to explore but if you want a comprehensive review of amination methodology this book is probably not for you.

Heather Tye*
University of Birmingham, UK

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