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Book Review Organic Synthesis Highlights II. Edited by H. Waldmann

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BOOKS
shown extending into the chemical symbols, making the latter difficult to read.
Broken-line bonds are sometimes missing
or are printed in varying styles, double
bonds in arenes are shown crookedly, ring
structures are also crooked in some cases
and the rings are often incomplete. The
symbols in equations are not all of uniform size. In the main text superscripts
and subscripts are a little too small, and
the latter are printed too low down. Otherwise, however, the text is very clearly set
out and easy to read.
The book provides a detailed and informative survey of synthetic methods for
hydrocarbons and their derivatives, including industrial processes. This very
useful compilation contains a wealth of
literature references. Its special appeal lies
in the excellent organization of the subject
matter. The most important chemical reactions of hydrocarbons, the mechanisms
involved, and the applications of these reactions in industrial processes are linked
together and described in a concise and
readable form. The book will be useful to
all readers with an interest in the reactions
of hydrocarbons as applied in industrial
processes. It will also serve as an excellent
foundation for newcomers to the petrochemical field and the chemistry of hydrocarbons, and for those switching interests
in these areas, especially as the industrial
processes described are identified by
name. Industrial chemists, research
chemists, and advanced students will also
find useful material in this concise and upto-date survey of all aspects of hydrocarbon chemistry.
Hans- Ullrich Siehl,
Alexander Christian Backes
Abteilung fur Organische Chemie I
der Universitat Ulm (Germany)
Organic Synthesis Highlights 11.
Edited by H. Waldmann. VCH Verlagsgesellschaft, Weinheim, 1995.407
pp., hardcover DM 148.00.-ISBN
3-527-29200-4
Organic synthesis is nowadays more
than ever before a meeting point of organic chemistry, biochemistry, biology,
medicine, physics,
sPaesis
and the material sciences. Books concerned with recent
u~t?’-m
developments
in
this area are therefore of considerable
interest to many
readers other than
1866
0 VCH
synthetic chemists. Organic Synthesis
Highlights II is a successor to the book
Organic Synthesis Highlights (J. Mulzer et
al.) published in 1990, also by VCH. It
contains 40 contributions based on a series of review articles published in the
journal Nachr. Chem. Tech. Lab. during
the period 1989-1993, under the general
title “Synthese im Blickpunkt”.
Eleven of the articles are by D. Schinzer
and twelve are by H. Waldmann, who has
also edited this volume. A further six articles are by M. Maier, and K. H. Dotz
appears as coauthor in another five. The
authors of the remaining contributions
are six industrial chemists: R. Bohlmann,
T. Brumby, H.-P. Fischer, P. Hammann,
R. Henning, and G. Sedelmeier. The book
is divided into two parts, the first dealing
with new methods and reagents for organic synthesis and the second with their applications in total syntheses of natural
products and analogs thereof.
Part 1 is concerned with six topical
themes of organic synthesis. The first of
these is asymmetric synthesis, to which six
chapters are devoted; the subjects range
from the Sharpless epoxidation and enantioselective cis-dihydroxylation, through
asymmetric aza-Diels- Alder reactions, to
the use of amines with C, symmetry as
chiral auxiliaries. The second topic is
organometallic chemistry, which is treated at considerable length in seven chapters, reflecting the growing importance of
organometallic reactions in synthesis. The
wide variety of topics covered includes
rhodium-catalyzed carbenoid cyclizations, nickel-activated C building blocks,
C-C bond-forming reactions using metallocenes of sub-group 4 metals, and aluminum enolates. The third group of articles is concerned with modern aspects of
organosilicon chemistry. In the three
chapters in this group the authors report
on selective transformations using pentacoordinated silicon compounds, oxidative
cleavage of silicon-carbon bonds, and the
temporary attachment of silicon-containing groups. The next group of articles has
the general heading “Enzymes in Organic
Synthesis”; here H. Waldmann reports on
applications of enzymatic catalysis in the
formation of C-C bonds and in syntheses
of 0-glycosides. The subject of the penultimate section of Part 1 is an “evergreen”:
the synthesis of heterocycles by cyclization reactions. In four chapters D. Schinzer deals very thoroughly with electrophilic
cyclizations of iminium, oxonium, and
sulfonium systems, and with the use of
polycyclization reactions in the synthesis
of alkaloids. Part 1 ends with five articles
on “General Methods and Reagents for
Organic Synthesis”. The methods dis-
VerlagsgrsellschaftmbH, 0-69451 Weinhemi, 1996
cussed here are domino reactions and
group-selective reactions, and the
reagents described are hypervalent iodine
species, furan as a synthetic building
block, and fluorine.
The articles in Part 2 describe total syntheses of natural products and active
agents. The discussions illustrate the impressive capabilities of the techniques now
available for organic synthesis, and also
emphasize the need to continually develop
new methods and reagents. The first of the
two sections contains most of the contributions from authors in industry, and is
concerned with syntheses of several important classes of natural products and
active compounds, including hydroxyethylene-isosteric dipeptides, natural
products for plant protection, penems, 0glycosides, carbacyclins, mitomycins, ergot and piperidine alkaloids, and taxanes.
The concluding part of the book-which
I might also describe as its crowning
achievement-is an account of the total
syntheses of several complex natural
products. Here the authors have chosen
some very interesting target molecules :
CC-1065, morphine, calicheamicin y:,
and rapamycin.
This list of topics is by no means complete, but is sufficient to show that the
book covers a wealth of modern developments in organic synthesis. Although the
articles treat such a wide variety of topics,
the quality is consistently high throughout. All the authors have succeeded in
presenting the essentials of their subjects
concisely and clearly. The reader needing
further details will benefit from the extensive lists of literature references.
Organic Synthesis Highlights I I will obviously be of great value for post-graduate
students and for everyone interested in
modern synthetic methods. It is also eminently suitable as a source for preparing
seminars and colloquia for advanced
undergraduate students. From the standpoint of students especially, it would of
course be helpful if this excellent book
could also be published in a cheaper paperback edition.
Uwe Beijiuss
Institut fur Organische Chemie
der Universitat Gottingen (Germany)
Theoretical and Physical Principles of
Organic Reactivity. By A . Pross. Wi-
ley, Chichester, 1995. 294 pp., hardcover 2 42.50.--ISBN
0-471-55599-1
Why do reactions have energy barriers?
That is the fundamental question addressed in this monograph by A. Pross,
O570-0833j96!3516-1R6 S 1S.OOf .2510
Angew. Chem. Int. Ed. Engl. 1996, 35, No. 16
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