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Erick M. Carreira and Lisbet Kvaerno Classics in stereoselective synthesis WileyЦVCH 2008 651 pp. d 60.0072

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Book Review
Published online in Wiley Interscience: 27 April 2009
( DOI 10.1002/aoc.1503
Book Review
Classics in stereoselective synthesis
Wiley–VCH, 2008, 651 pp.
price £ 60.00/£72.00 (paperback)
Classics in Stereoselective Synthesis
deserves to be highlighted as one
of the best books on asymmetric
synthesis available to the chemical
community. It is certainly one
of the most comprehensive and
readable texts in the area, which in
itself is no mean feat considering
the amount of material there is
and continues to be. This in itself
poses the first question on how
you define a classic. The authors
themselves grapple with this in the
preface, suggesting that calling
something ‘classic’ means that it is no longer used (as in the
‘Classic’ languages) and one gets the feeling that they question
whether they should be using the term in the first place. ‘Classic’
for me, however, refers to something that is timeless because it
has evolved and proved adaptable. So, just as modern languages
are an iteration of the old ones, so the synthetic ‘classics’ continue
to be used today – over and above the applications for which they
were invented. No sooner has someone designed an excellent
asymmetric catalyst then someone else has developed it to work
in water, for example. ‘Classic’ then refers to something which
will never stop being used. Indeed the authors have managed
heroically to include all those reactions that fall within that
definition – and there are many.
The cover of the book is of standard Wiley format and there
is a sketch of a model holding up two hands, both of which
are overlaid with a tetrahedron. Although not eye-catching in a
Dan Brown sort of way (thankfully), the significance of the sketch
upon stereochemistry is obvious and it makes a change to the
slightly prosaic structures of catalysts and auxiliaries that one
normally sees on books of this subject. The preface, though a little
overzealous in its use of quotation (some slightly out of context)
lays out the importance of the field, as well as what the authors
are trying to achieve with this book. The chapters themselves are
divided logically with titles such as ‘Carbonyl addition reaction’
and ‘Reduction of olefins’. The ordering of chapters seems less
logical, but this is immaterial as it really has no negative effect on
the book itself.
The schemes and figures are generally useful and aid the
text considerably as one would expect in an organic chemistry
textbook. However, one criticism would be that are not enough
captions associated with these diagrams. This would have been
useful for the person who likes to just flick through the book
rather than having to read reams of text to find the associated
paragraphs. Indeed, Nicolaou and Sorensen in their book Classics
in Total Synthesis from the same publishers use boxes to good
effect in explaining basic mechanisms and this book might have
benefited from such an approach. This leads on to one other
point, which is that of mechanisms and how occasionally it would
have been useful to have more of them within the text. For the
asymmetric chemist, it is not enough to know that A goes to
B; they need to know why. Again, however, the authors explain
in the preface that they have only done so where they felt it
would be ‘particularly valuable for understanding or predicting
the observed stereochemistry’. They have a point, because overall
the flow of the text works well as it stands, and with too much
mechanistic detail it may have felt slightly jarring (and the book
would probably have been double the size).
As mentioned at the beginning of this review, the field of
asymmetric synthesis is very large indeed and deciding what is a
‘classic’ is a very difficult task. No wonder then that there should
be some omissions, such as enzyme-mediated processes, or some
areas that are a little light on content, such as aziridinations.
Nevertheless, the authors have created a book which will take
some beating in terms of breadth and depth and which should
take a position on every organic chemist’s bookshelf for a very
long time indeed.
André Cobb
University of Reading, Reading, UK
Appl. Organometal. Chem. 2009 , 23, 251
c 2009 John Wiley & Sons, Ltd.
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stereoselective, 2008, carreira, synthesis, classic, lisbeth, eric, wileyцvch, 0072, 651, kvaerno
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