Dynamic Stereochemistry of Chiral Compounds: Principles and Applications - Rilegato

Wolf, Christian

Rilegato

ISBN 10: 0854042466 ISBN 13: 9780854042463

Casa editrice: Royal Society of Chemistry, 2007

Riassunto

This book provides an overview of fundamental concepts of asymmetric synthesis highlighting the significance of stereochemical and stereodynamic reaction control. Topics include kinetic resolution (KR), dynamic kinetic resolution (DKR), dynamic kinetic asymmetric transformation (DYKAT), and dynamic thermodynamic resolution (DTR). In-depth discussions of asymmetric synthesis with chiral organolithium compounds, atropisomeric biaryl synthesis, self-regeneration of stereogenicity (SRS), chiral amplification with chiral relays and other commonly used strategies are also provided. Particular emphasis is given to selective introduction, interconversion and translocation of central, axial, planar, and helical chirality. A systematic coverage of stereochemical principles and stereodynamic properties of chiral compounds guides the reader through the book and establishes a conceptual linkage to asymmetric synthesis, molecular devices that resemble the structure and stereomutations of propellers, bevel gears, switches and motors, and topologically chiral assemblies such as catenanes and rotaxanes. Racemization and diastereomerization reactions of numerous chiral compounds are discussed as well as the principles, scope and compatibility of commonly used analytical techniques. Details of analytical methods are provided and discussed as well as topics relating to the design of fascinating topologically chiral assemblies and molecular technomimetic devices in the context of dynamic stereochemistry. Strategies and recent developments that address important synthetic challenges are presented and highlighted with hundreds of examples, applications and detailed mechanisms. This exceptional book includes: - More than 550 figures, schemes and tables illustrating mechanisms of numerous asymmetric reactions and stereomutations of chiral compounds - Technical drawings illustrating the conceptual linkage between macroscopic devices such as turnstiles, ratchets, brakes, bevel gears or knots and molecular analogs - More than 3000 references to encourage further reading and facilitate additional literature research - A comprehensive glossary with stereochemical definitions and terms which facilitate understanding and reinforce learning This book will be of particular interest to undergraduates, graduates and professionals working and researching in the fields of organic synthetic chemistry and analytical chemistry.

Su questo libro

Recensione:

Asymmetric synthesis

Dynamic stereochemistry of chiral compounds: principles and applications
Christian Wolf
RSC Publishing, Cambridge, UK
2008, 512pp, (HB) ISBN 9780854042463

Reviewed by David Amabilino

When searching for texts on asymmetric synthesis, this book might not be the first one I would pick up, judging by its title alone - yet it principally deals with just that. It offers an overview of the most important aspects of introducing, interconverting, and translocating chirality in the preparation of compounds (mainly organic, although coordination and organometallics are touched on) and closely related topics, including contemporary challenges.

Seeing the words 'stereochemistry' and 'compounds' in the title makes one think immediately of Eliel, Wilen and Mander's massive work Stereochemistry of organic compounds; it is impossible not to. Although Wolf's book in no way challenges that masterpiece, I feel it is presented in a way which gives a uniquely bright outlook on particular aspects, and lays down a contemporary, concise, coherent and entertaining romp through dynamic stereochemistry. The only omission (as the authors freely admit) which disappointed me a bit, is materials-related stereochemistry: polymers and liquid crystals are ruled out through restrictions of space.

There are three main parts to the book. The first is a brief introduction to general stereochemistry and to dynamics, with a discussion of the principles behind phenomena such as racemisation and diastereomerisation. The second part deals mainly with asymmetric synthesis, including the application of stereodynamic systems in the area. Finally, stereodynamic devices and molecular machines, as well as topological stereochemistry, are discussed.

The book is well produced, very clear and readable, with a particularly comfortable format. A basic knowledge of stereochemistry is required, but I would recommend the work for advanced students - masters and doctoral stage researchers - as well as the broad-minded professional.

Chemistry World, 2008, 5(4), p.p. 75-76

L'autore:

Professor Christian Wolf graduated from the University of Hamburg, Germany in 1993 where he received his Ph.D. in 1995 under the auspices of Professor Wilfried A. K÷nig. After working as a postdoctoral Feodor-Lynen Fellow with Professor William H. Pirkle at the University of Illinois in Urbana, Illinois he took an R&D position at SmithKline Beecham Pharmaceuticals, King of Prussia, Pennsylvania in 1997. In 2000, he accepted a position as Assistant Professor in the Chemistry Department at Georgetown University in Washington, DC where he was promoted to Associate Professor with tenure in 2006. He has been a visiting scholar at the University of Reading, England in 1991 and at the University of Aix-Marseille, France in 1995. Professor Wolf's research interests comprise stereodynamics of chiral compounds, asymmetric synthesis, stereoselective sensing, chiral recognition, transition metal-catalyzed cross-coupling reactions, development of antimalarial drugs, and chiral chromatography.

Su questa edizione

• Editore: Royal Society of Chemistry
• Data di pubblicazione: 2007
• ISBN 10: 0854042466
• ISBN 13: 9780854042463
• Rilegatura: Copertina rigida
• Numero di pagine: 512