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Allylic boron compounds have gained a prominent position as a truly practical class of synthetic reagents in the past twenty-five years. Their main application as a method for the stereoselective synthesis of homoallylic alcohols by allyl-transfer to carbonyl compounds is essentially unmatched. In this process, a new carbon-carbon bond is formed, and up to two new stereogenic centers are created in a predictably controlled manner. Highly effective and general enantioselective variants are available, with countless applications in the total syntheses of polyacetate and polypropionate natural products. Furthermore, the residual allylic unit can be manipulated through a number of different transformations such as oxidative cleavage, olefin metathesis, hydrometalations, and many others. The discovery of Lewis and Brønsted acid catalyzed manifolds recently, has opened new doors for further development of this important reaction. This book provides an up-to-date, comprehensive survey of the literature of this rich chemistry as it pertains to organic synthesis. Consistent with the goal of Organic Reactions, the content and presentation emphasize the preparative aspects of the reactions, giving considerable attention to the scope and limitations of the individual transformations along with detailed experimental procedures. A tabular survey of all examples of carbonyl allylboration used in organic synthesis is presented in nine tables organized by type of allylic boron reagent with listings within each table according to increasing carbon number of the carbonyl substrates. The literature is covered through December 2010, including a new listing of nearly 200 literature citations that supplement the original coverage of 834 references used in the earlier hard cover version of the chapter. Allylboration of Carbonyl Compounds is intended to be a useful, easily read reference book for all practitioners of synthetic organic chemistry working in academic and industrial laboratories.
Spurred by the desire to make chemistry a sustainable and "greener" technology, the field of organocatalysis has grown to become one of the most important areas in synthetic organic chemistry. Organic catalysts can often replace potentially toxic metal catalysts and allow reactions to proceed under mild reaction conditions, thereby saving energy costs and rendering chemical processes inherently safer. More importantly perhaps, organocatalysis offers a complementary reactivity in many instances leading to increased versatility.This Handbook describes 126 key reagents for organocatalytic reactions and will be especially useful for professionals in the area of sustainable chemistry, medicinal research, as well as synthetic organic chemists working in academia and the pharmaceutical industry. All the information compiled in this volume is also available in electronic format on Wiley Online Library. The 126 reagents represented here are but a small fraction of the ca. 5,000 reagents available in the electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS). e-EROS offers various search interfaces to locate reagents of interest, including chemical structure, substructure and reactions search modes. e-EROS is updated regularly with new and updated entries.
Written by highly renowned and experienced authors, this is the only reference on the application of solvents as reagents. Clearly structured, the text describes various methods for the activation and reaction of these small molecules, highlighting the synthetic opportunities as well as process-oriented advantages. To this end, all relevant types of solvents are covered separately and emphasized with numerous synthetic examples, while taking care to explain applications so as to avoid undesired side reactions. The result is a unique resource for every synthetic chemist and reaction engineer in industry and academia working on the methodical optimization of synthetic transformations.
Since its discovery in 1963 by R. B. Merrifield, solid-phase synthesis, or polymer-supported synthesis, has become an essential technique with its wide use in the synthesis of peptides and other oligomers. Solid-Phase Reactions provides extensive and comprehensive information on this form of synthesis in a format ideal for those working in the laboratory. As part of the Handbook of Reagents in Organic Synthesis Series, this new addition extends the wealth of information available to the chemist at the bench. All content has been expertly collected and presented by an internationally recognised and respected editorial board led by Professor Peter Wipf.
Over the last three decades the importance of organosiliconchemistry has greatly increased because it has opened a number ofnew synthetic strategies. Silicon reagents are usually low-cost,versatile and allow a wide range of reactions. This is the firstHandbook to compile essential Silicon containing reagents and makesuse of the leading reagent database e-EROS. Another hotvolume in the series Handbooks of Reagents for OrganicSynthesis, this is a must-have resource for all syntheticchemists working in drug development and medicinal chemistry. For the selection the Editor focussed on three key syntheticapproaches with the greatest impact: 1. Use of silicon as a 'temporary tether' by unifying a reactivepair of functional groups and taking advantage of theirtemplate-biased intramolecular cyclization. 2. The specific use of the silane functionality as a heterot-butyl group, often colloquially referred to as the use ofsilicon as a 'fat proton'. 3. The use of the Brook rearrangement as an 'anion relaystratagem'. A new feature in this Handbook is the reagent finder, analphabetically organized lookup table arranged by organicfunctionality and specific structure of the silicon atom to whichit is bound.