EnantioselectiveChemical Synthesis

The development of efficientenantioselective methods for the

synthesis of complex organic mole-cules, in particular of natural products

and pharmacologically relevant analogs,has made breathtaking progress in the past

few decades. The speed of scientific develop-ment, especially in the area of asymmetric organicand metallo-organic catalysis, and the multitude ofpublications (including specialized reviews andmonographs) makes it difficult for students,researchers, and teachers to keep track of advances,to be aware of the latest possibilities when planninga synthesis, and to adequately evaluate new pub-lications.

Against this background, the book by Coreyand K�rti undertakes the very welcome anddifficult attempt to compile the “most importantand useful” methods of enantioselective synthesis,first in encyclopedic form (Part 1, 150 pages), thenby introducing some strategic concepts for theplanning of enantioselective syntheses (Part 2, 20pages), and finally by describing nearly fifty totalsyntheses as examples (Part 3, 150 pages).

At first sight, the very attractively designedbook, with some figures in color, a well-arrangedstructure, clear graphic formulas and reactionschemes, and an enormous number of references,creates a very good impression. A second lookreveals that the book—like an earlier monographby the first author and Nobel laureate E. J. Corey(The Logic of Chemical Synthesis, John Wiley &Sons, 1990)—emphasizes the author�s scientificcontributions to an appreciable extent. Thus, thesyntheses described as examples are a compilationof total syntheses carried out in Corey�s laboratoryin the past two decades, and the references (and thelist of methods introduced in Part 1) are also by nomeans complete, but reflect a personal choice bythe authors.

The reader who is aware of these limitationsand does not regard this book as a “referencesource”, but is willing to look at the world ofenantioselective synthesis through the eyes ofsynthesis grandmaster E. J. Corey, will be rewardedwith many interesting, stimulating, and helpfulinsights. And in that manner the book fully servesits purpose.

Part 1 presents many important chirogenicsynthetic transformations in a clear manner,arranged under methods for the formation of C�H, C�O, C�N, C�Y, and C�C bonds. A separatesection deals with cycloadditions and other cycliza-tion reactions. Within this thoughtfully chosenstructure, the authors present a relevant selectionof useful enantioselective protocols, with the focus

appropriately placed on catalytic systems, whereasonly a few auxiliary-based methods are mentioned.The general concepts are always illustrated with anumber of well-chosen examples, and the structuresof the necessary chiral catalysts and ligands areshown separately. Even though some renownedspecialists will search in vain for their own con-tributions, the compilation reflects the present stateof the art in the area of asymmetric organic andmetallo-organic catalysis in an impressive andconvincing manner. The only cause for regret isthat biocatalytic (enzymatic) methods are notcovered at all.

Part 2 of the book ties in directly with thealready mentioned work The Logic of ChemicalSynthesis, and begins with a brief recapitulation ofCorey�s terminology of retrosynthesis and thevarious transform types, before introducing variousconcepts for the stereo-controlled building ofcomplex structures. Selected examples are descri-bed to illustrate how the examination of highly-ordered pre-transition-state assemblies makes itpossible to rationalize and/or predict the stereo-chemical course of enantioselective processes.

Part 3 presents a multitude of total syntheses,showing in each case the complete reaction scheme(including reaction conditions and yields), followedby a description of the underlying retrosyntheticplan. In many cases the stereoselectivity is high-lighted. Each section is rounded off by a shortexplanation of the importance of the target mole-cule and a summary of the key steps of thesynthesis. A table at the beginning of Part 3 givesan overview of all the target structures, which notonly makes it easy for the reader to navigatethrough the contents but also illustrates the greatstructural variety and complexity of the (predom-inantly polycyclic) natural products that Corey andco-workers have successfully synthesized in thepast years. The crystal-clear descriptions of thesyntheses and the genius displayed in the manner ofachieving them, as well as their orderly classifica-tion, make this part a real treasure-trove ofstimulating ideas, and they offer ideal case-studiesfor advanced lectures and seminars in organicsynthesis.

Anybody who chooses to do so may criticize thebook for its (intentional) subjectivity. But really wemust raise our hats to the authors who havecollected an enormous wealth of information andprepared it in a well-arranged manner. The ratherterse and economical presentation of the material,and the way in which it is rationalized with the helpof tables, certainly sets an interesting standard, andis appropriate in our world that is so used tocolorful visual signals.

It is beyond question that this comprehensive,stimulating, and highly up-to-date book is worththe price and will get a wide distribution. It

Enantioselective ChemicalSynthesisMethods, Logic and Practice.By Elias J. Corey and L�szl�K�rti. Direct Book Publish-ing, 2010. 334 pp., hard-cover, $ 75.00.—ISBN 978-0615395159

Books

2887Angew. Chem. Int. Ed. 2011, 50, 2887 – 2888 � 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

deserves its place on the bookshelves of all who areinterested in synthesis. It will surely be a long timebefore this book, as part of the scientific legacy of agreat pioneer of chemical synthesis, begins togather dust in our libraries.

Hans-G�nther SchmalzDepartment of ChemistryUniversity of Cologne (Germany)

DOI: 10.1002/anie.201100655

4D ElectronMicroscopy

The renowned authors of thisnew appearance on time-resolved

3D electron microscopy have cre-ated a fantastic book that will appeal to

a broad range of scientists. Its topic andbreadth will surely be of interest to those

interested in physics, material science, and solid-state chemistry. The attraction of this book stemsfrom the deep knowledge of the authors, who areclearly the leaders in the field. On the one hand,there are currently only a few labs that areexperimenting with 4D electron microscopy, buton the other hand, everybody is talking about it.The expertise of the authors and the clear, well-documented nature of the book combine to lend itgreat potential to set the standard in this field.

Time-resolved spectroscopy and electronmicroscopy are familiar to many potential readers.This book describes the combination of aspects ofboth subjects in this completely new and excitingfield. While the book and the topic it covers breaknew scientific ground, the authors take care tomake their work accessible to a broad readership. Itis well-structured and includes many referenceswith background information for readers outsidethe field. Different facets of the complex subjectmatter are well balanced, and aspects likely to beunfamiliar to many readers are explained with care.It is clear that experienced book writers were atwork.

To fully understand the content, a degree ofbackground knowledge in optics, solid-state phys-ics, and quantum mechanics is necessary. Never-theless, I have the feeling that less qualified orexperienced readers will also be interested in thebook. Its general appeal is attested to by my ownexperience: As the book was lying on my deskwhile I prepared this review, nearly every youngresearcher entering my office, regardless ofwhether his or her background was in biology,mineralogy, or solid-state physics, had a look at itand showed interest, usually with the remark:“When you finish it, could I have a look?”

Gustaaf Van TendelooEMAT research groupUniversity of Antwerp (Belgium)

4D Electron MicroscopyImaging in Space and Time.By Ahmed H. Zewail andJohn M. Thomas. ImperialCollege Press, 2010. 360 pp.,softcover, £ 36.00.—ISBN978-1848164000

Books

2888 www.angewandte.org � 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Angew. Chem. Int. Ed. 2011, 50, 2887 – 2888