![]() |
![]() |
|||||||
3base
(Hive Bee) 07-09-02 18:46 No 330444 |
![]() |
modern amination methods | Bookmark | |||||
Modern Amination Methods. Edited by Alfredo Ricci (University of Bologna). Wiley-VCH: Weinheim. 2000. xvii + 268 pp. $168. ISBN 3-527-29976-9. 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 presented. 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 editor’s 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 JA015212Q 10.1021/ja015212q J Am Chem Soc, 2001 123(27): 6744-6744 "Book Review: Modern Amination Methods" Edited by Alfredo Ricci |
||||||||
![]() |
![]() |
|||||||