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Modern Amination Methods. Edited by Alfredo Ricci (University
of Bologna). Wiley-VCH: Weinheim. 2000. xvii + 268 pp. $168.
Organonitrogen compounds, and amines in particular, are immensely
important as chemical intermediates and end-products, especially in
the pharmaceutical and agricultural industries. As such, reactions that
form C-N bonds are of great significance. This book includes seven
chapters by prominent researchers in the field who review recent
developments in the synthesis of amines but emphasize non-substitution
reactions and stereoselective methods.
In the first chapter, K. A. Jorgensen reviews newer aspects of allylic
amination methods, including nucleophilic amination of allylic elec-trophiles,
and direct aminations of olefins, including ene-type and metal-promoted
amination reactions. Illustrative examples are given, but
extensive tables are not. In Chapter 2, E. Fernandez and J. M. Brown
discuss electrophilic amination routes from alkenes, emphasizing net
hydroaminations via hydroboration/ammonolysis. Little coverage of
metal-promoted hydroamination is provided, despite the substantial
activity in this area over the past decade. In Chapter 3, J.-P Genet, C.
Greck, and D. Lavergne summarize developments in the area of
electrophilic amination of olefins and enol derivatives (ene-type
reactions) by sulfonoxycarbamates and azodicarboxylates, emphasizing
diastereo- and enantioselective transformations. In the next chapter,
H. Tietgen, M. Schultz-Kukula, and H. Kunz draw substantially on
their own work to summarize the use of glycosylamines as chiral
auxiliaries (usually via imine derivatives) in the stereoselective synthesis
of chiral amines, particularly amino acids and heterocycles. C. S.
Tomooka, H. Iikura, and E. M. Carreira then cover in Chapter 5 the
synthesis of transition metal-nitride complexes (organized by metal).
This topic only indirectly fits within the book title theme; however,
these compounds are of interest synthetically as potential N-transfer
agents, which are covered in Chapter 6. In Chapter 6, S. Minakata and
M. Komatsu discuss asymmetric N-transfer reactions of olefins and
enol derivatives with nitrido-Mn complexes. Included is a disappoint-ingly
brief coverage of aziridinations via other metal-nitrenoid reagents
(e.g., Cu-catalyzed aziridinations) and more complete coverage of the
synthesis and stoichiometric reactions of achiral and chiral salen-Mn-
nitrido complexes, which generally provide aziridines (or R-amino
ketones from enol derivatives). Finally, J. F. Hartwig provides an
extensive review of Pd-catalyzed aminations of aryl electrophiles. This
very active area is covered from a historical perspective, and first-,
second-, and third-generation catalysts are discussed in terms of
improved efficiency and scope. Extensive tables are provided that
summarize yields with various substrates, aminating agents, and
catalysts; applications of these reactions to various areas and a
discussion of the state of their mechanistic understanding are also
Overall, the focus of this work is a timely one that should be of
interest to a broad segment of the synthetic organic community. By
the editorís own admission, "no attempt has been made to present a
comprehensive work". As could be expected from such a multiauthored
compendium, there are some significant gaps in the coverage of topics,
most notably in the areas of copper-catalyzed asymmetric aziridination
and metal-catalyzed hydroamination and amino-hydroxylation reactions.
Nonetheless, these are generally good quality, mid-depth, reasonably
up-to-date reviews (most of the chapters contain references through
1999) of many of the active areas in synthetic methods development
for amines. The quality of the text and graphics is very good, with few
typos detected. The book should be in the libraries of all institutions
where synthetic organic chemistry is practiced as well as in the personal
libraries of those who wish to keep abreast of developments in the
synthesis of amines.
Kenneth M. Nicholas, UniVersity of Oklahoma, Norman
J Am Chem Soc, 2001 123(27): 6744-6744
"Book Review: Modern Amination Methods"
Edited by Alfredo Ricci