Wiley Catalysis in Asymmetric Synthesis (Postgraduate Chemistry Series)

Asymmetric synthesis has become a major aspect of modern organic chemistry. The stereochemical properties of an organic compound are often essential to its bioactivity, and the need for stereochemically pure pharmaceutical products is a key example of the importance of stereochemical control in organic synthesis. However, achieving high levels of stereoselectivity in the synthesis of complex natural products represents a considerable intellectual and practical challenge for chemists. Written from a synthetic organic chemistry perspective, this text provides a practical overview of the field, illustrating a wide range of transformations that can be achieved. The book captures the latest advances in asymmetric catalysis with emphasis placed on non-enzymatic methods.Topics covered include:Reduction of alkenes, ketones and iminesNucleophilic addition to carbonyl compoundsCatalytic carbon-carbon bond forming reactionsCatalytic reactions involving metal carbenoidsConjugate addition reactionsCatalysis in Asymmetric Synthesis bridges the gap between undergraduate and advanced level textbooks and provides a convenient point of entry to the primary literature for the experienced synthetic organic chemist. About the Author Dr Vittorio Caprio Lecturer in Organic and Medicinal Chemistry in the Department of Chemistry, University of Auckland, New Zealand. His research interests lie in the application of synthetic organic methods to the synthesis of bioactive natural products of diverse structure. A central aim is the efficient and elegant syntheses of target core structures in a stereocontrolled manner using nature as the source of chirality. The ultimate goal is to use natural medicines as the basis for designing and synthesizing drugs of greater therapeutic value.  Professor Jonathan MJ Williams (author of the first edition)Department of Chemistry, University of Bath, UKResearch involves with the use of transition metals for the synthesis of useful organic molecules.  In particular, we have been developing reactions using ‘borrowing hydrogen.’  In this chemistry, ruthenium or iridium catalysts temporarily remove hydrogen to give an aldehyde.  This aldehyde then reacts to give an alkene (or imine) and the hydrogen is then returned to give a C-C or C-N bond.  These procedures allow alcohols to be used as alkylating agents in place of more conventional, but often toxic/mutagenic alkyl halides. Excerpt. © Reprinted by permission. All rights reserved. Catalysis in Asymmetric SynthesisBy Vittorio Caprio Jonathan WilliamsJohn Wiley & SonsCopyright © 2009Vittorio Caprio and Jonathan M.J. WilliamsAll right reserved.ISBN: 978-1-4051-9091-6Chapter OneIntroduction There are several ways of producing compounds as single enantiomers. The resolution of a mixture of enantiomers can often be the cheapest, most practical way of obtaining enantiomerically pure material. The conversion of a cheap enantiomerically pure starting material into another derivative represents another useful technique in some cases. However, asymmetric synthesis can provide a more general approach to the preparation of enantiomerically enriched compounds. Asymmetric synthesis is limited by the range and scope of available methodology. Fortunately, with so much research in the area, there are many methods now available, with further asymmetric reactions being developed each year. There may still be cases where asymmetric synthesis doesn't provide the best method for the preparation of a particular enantiomerically pure compound, but it certainly allows for the preparation of a more diverse range of structures. Asymmetric catalysis is an especially appealing aspect of asymmetric synthesis. Small amounts of a catalyst (frequently less than 1 mol%) can be used to control the stereochemistry of the bulk reaction. The use of a catalyst often makes the isolation of a product easier, since there is less unwanted material to remove at the end o