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Book Review Modern Synthetic Methods 1992. Vol. 6. Edited by R. Scheffold

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BOOK REVIEWS
Modern Synthetic Methods 1992. Vol. 6. Edited by R. Schefi
.fold. Verlag Helvetica Chimica Acta, Basel/VCH Verlagsgesellschaft, Weinheim/VCH Publishers, New York, 1992.
489 pp., hardcover DM 108.00.-ISBN 3-906390-00-4/3527-28489-311-56081-255-9
The 6th International Symposium on Modern Synthetic
Methods was held on the 4th and 5th of May 1992 in Interlaken. The proceedings volume of this latest in a well-established series of symposia contains reviews on the following
topics : “Regio- and Stereoselective Formation of Enolates
and the Consequences of Enolate Configuration and Subsequent Reactions”, by C. H. Heathcock; “Acetylenes in Synthesis”, by E. Winterfeldt; “Superbases as Powerful Tools in
Organic Synthesis”, by M. Schlosser; “Enantiopure Building Blocks from Sugars and their Utilization in Natural
Product Synthesis”, by F. W Lichtenthaler; “Carbohydrate
Synthesis via Thiazoles”, by A. Dondoni; and “Protective
Group Strategies in the Synthesis of Functionalized Carbohydrates”, by C. A. A. van Boeckel.
All the contributions reflect the latest state of knowledge,
with detailed literature references extending up to 1991. The
convenient arrangement of subject matter and the clear
schemes make for easy reading. It is pleasing to note that, as
a general rule, a reaction arrow represents only a single
transformation. All the articles except the one on alkynes
contain many examples of laboratory recipes, which enable
one to work through the syntheses. Unlike previous volumes
there is, for the first time, a subject index, which is a valuable
aid when using the book.
C. H. Heathcock gives a lucid overview of the chemistry of
enolates. from its beginnings up to the present state of
knowledge. Reactions leading to regio- and stereoselective
formation of enolates are discussed in detail. The author
then describes the influence of the configuration of enolates
on the stereochemistry of subsequent reactions, especially
aldol additions.
E. Winterfeldt reports on the latest developments in the
use of alkynes in synthesis. These include thermal and
organometallic reactions of alkynes, such as [271 + 2nI-cycloadditions, 1,3-dipolar additions, Diels-Alder, en, and pericyclic reactions, free radical and carbene reactions, and reactions of organometallic compounds. Some applications of
ionic reactions of alkynes are also described.
M. Schlosser deals with the preparation and synthetic applications of superbases. Methods-for forming metalkarbon
bonds and for activating metal compounds by forming
superbases are described, as well as the use of superbases in
An,~yir.C ’ h i , n i . lrit Ed. EnEl. 1992, 31. N o . 10
achieving metalation at aliphatic, olefinic, and heterocyclic
positions. The review is completed by examples of arene
metalations influenced by neighboring groups, and of regioand stereocontrolled reactions of allylic carbanions prepared
from superbases.
The use of cheap carbohydrates as precursors for the
preparation of enantiomerically pure synthetic building
blocks, and their applications in natural products syntheses,
are discussed by F. W. Lichtenthaler. The emphasis is on
syntheses using simple, easily obtainable reagents and protecting groups, and on avoiding the need for laborious workup procedures.
A. Dondoni devotes his contribution to the synthesis of
carbohydrates by the addition of aldehydes to thiazole
derivatives. By means of this versatile synthetic strategy one
can, in a stepwise procedure, stereoselectively build up the
carbon skeleton of a sugar around one, two, or three carbon
atoms by combining a suitable 2-substituted thiazole derivative with an aldehyde.
C. A. A. van Boekel describes syntheses of biologically
active oligosaccharides, in particular of heparin fragments.
The regio- and stereoselective synthesis of these highly functionalized molecules is achieved by the clever use of appropriate protecting group techniques and glycosidation methods.
Each of these articles provides an excellent overview of the
topic covered, and offers a rapid way into it for the newcomer. The book can therefore be recommended unreservedly
for all synthetic chemists and also for advanced students,
and it should be in every chemical library. The sturdy binding (an improvement on the previous paperback volumes)
and the careful preparation of the volume, including the
index, complete the favorable overall impression.
Fritz Theil
Zentrum fur Selektive Organische Synthese
Berlin-Adlershof (FRG)
Design and Optimization in Organic Synthesis. (Series: Data
Handling in Science and Technology, Vol. 8.) By R. Curlson. Elsevier, Amsterdam, 1991. XVI, 536 pp., hardcover
HFI 330.00.-ISBN 0-444-89201-X
During the last few years many books on the design of
experiments have been virtually thrown onto the market. It
is all the more pleasing, therefore, that Rolf Carlson has
allowed time for his contribution to the subject to mature,
and has produced a book that is excellent from both the
pedagogic and scientific standpoints. It is by no means merely “ ... yet another introductory text on statistics written by
a non-statistician”, as Carlson, who is himself an organic
chemist at the University of Umea, the stronghold of chemometrics in Sweden, fears in his preface that it might be
judged.
This book of around 500 pages includes a brief but comprehensive index, a detailed bibliography, references to suitable software, about 30 pages of tables, a few graphics, and
a number of detailed examples. There are 19 chapters, six of
which might be described as the essential core of the book:
“Models as tools” (Ch. 3), “Two-level factorial designs” and
“Two-level fractional factorial designs” (Chs. 5 and 6), “Response surface methods” (Ch. 12), “Principal properties”
(Ch. 15), and “Quantitative relations between observed responses and experimental variations” (Ch. 17).
VCH VerlagrgesrlfschufrmbH, W-6940 Weinhrim, 1992
057n-0833~92j1010-13933 3.50+ ,2530
1393
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