Domino reactions: concepts for efficient organic synthesis

Svetlana Borukhova

doi:10.1515/gps-2014-0078

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Domino reactions: concepts for efficient organic synthesis

Svetlana Borukhova

Published/Copyright: November 20, 2014

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From the journal Green Processing and Synthesis Volume 3 Issue 6

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Tietze Lutz F. Wiley-VCH 2014 Hardcover, 648 pp. € 149.00 978-3-527-33432-2

Most of the times, the moment we see a complex target molecule we begin with its stepwise retrosynthesis. We look at the functional groups, and based on their activity we split the molecule into starting compounds. Later, we think of each transformation separately, and step-by-step move forward to reach the final design of the total synthesis. Alternatively, so-called “domino” reactions can be implemented. Domino reactions, as the name suggests, incorporate two or more bond formations under the same conditions, which involve the subsequent transformations of functionalities formed in the previous reaction steps. The approach offers a higher complexity of the final product, higher efficiency and atom economy, less generation of waste, and lesser use of resources, be it materials, energy, time or money. This strategic approach to synthesis was first introduced by the editor of the current book, Tietze. It started with the synthesis of secologanin aglucon, where hetero Diels-Alder reaction was coupled to the synthesis of the heterodiene via a Knoevenagel condensation of a β-dicarbonyl compound and an aldehyde. This way the first domino-Knoevenagel hetero Diels-Alder reaction took place. Since then, the strategy has been extended to a wider scope of reactions. The most impressive examples presented by 33 contributors from all over the world are collected in the current book titled “Domino reactions: concepts for efficient organic synthesis” edited by Tietze.

The book consists of 15 chapters, which differ in the mechanism of the steps involved, the type of processes used and the type of products synthesized. The mechanisms covered are carbonylation based transition metal catalysis, metathesis, CH-activation, nucleophilic substitutions, radical reactions, pericyclic reactions, Michael reactions, aldol reactions, oxidations and reductions. Processes, such as organocatalysis, enantio- and diastereoselective reactions, and multicomponent reactions as well as domino processes under microwave irradiation, high pressure and those carried out in water are discussed. The last three chapters cover the applications of domino reactions in library synthesis, total synthesis of natural products, and strategies involved in transforming multicomponent synthesis into domino processes.

Except some, all chapters provide the reader with a clear and concise introduction to the mechanisms involved, making the text graspable for a wider audience than only organic synthetic chemists. The introduction of the subject is followed by a well-structured presentation of the most impressive and inspiring examples along with corresponding references. Moreover, the conditions, nature and the number of substrates along with outcomes are included within the schematic representations of the examples. Thus, whether it is a specific structure or mechanism you would like to investigate, you will find your way easily within the book.

Finally, this book once again elucidates the way to rethink the conventional stepwise synthetic routes of complex structures. The concept domino principle is fascinating, therefore with the nowadays progressive technology and interdisciplinary backgrounds of scientists its implementation should be more realizable for the production of block-busters and other widely used complex molecules. To conclude, the book will cater well to organic synthetic chemists, along with bio- and chemical engineers. It is also suitable as a reference and an additional textbook in the Organic Chemistry course.

Published Online: 2014-11-20

Published in Print: 2014-12-1

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

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