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Asymmetric Organocatalysis

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ISBN 10: 3642028144 / ISBN 13: 9783642028144
Published by Springer-Verlag Gmbh Mrz 2010, 2010
New Condition: Neu
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Neuware - As nucleophiles, simple alkenes are typically so unreactive that only highly active electrophiles, such as carbocations, peroxides, and halogens will react with them. For the generation of carbon-carbon bonds, milder methods will often be required. Fortunately, it is possible to increase the reactivity of alkene-type p-nucleophiles by introducing electron-donating substituents. Substitution of one H with an OH or OR gives an enol or a vinyl ether, which are already much better nucleophiles. Using nitrogen instead of oxygen, one obtains even better nucleophiles, enamines. Enamines are among the most reactive neutral carbon nucleophiles, exhibiting rates that are even comparable to some charged nucleophiles, such as enolates [1, 2]. Most enamines, unfortunately, are sensitive to hydrolysis. The parent enamine, N,N-dimethylvinylamine, has in fact been prepared [3], but appears to be uns- ble. Enamines of cyclic ketones and many aldehydes can readily be isolated, however [4 7]. The instability of enamines might at first appear to diminish the utility of enamines as nucleophiles, but actually this property can be viewed as an added benefit: enamines can be readily and rapidly generated catalytically by using a suitable amine and a carbonyl compound. The condensation of aldehydes or ketones with amines initially affords an imine or iminium ion, which then rapidly loses a proton to afford the corresponding enamine (Scheme 1). 400 pp. Englisch. Bookseller Inventory # 9783642028144

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Bibliographic Details

Title: Asymmetric Organocatalysis

Publisher: Springer-Verlag Gmbh Mrz 2010

Publication Date: 2010

Binding: Buch

Book Condition:Neu

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Synopsis:

As nucleophiles, simple alkenes are typically so unreactive that only highly active electrophiles, such as carbocations, peroxides, and halogens will react with them. For the generation of carbon-carbon bonds, milder methods will often be required. Fortunately, it is possible to increase the reactivity of alkene-type p-nucleophiles by introducing electron-donating substituents. Substitution of one H with an OH or OR gives an enol or a vinyl ether, which are already much better nucleophiles. Using nitrogen instead of oxygen, one obtains even better nucleophiles, enamines. Enamines are among the most reactive neutral carbon nucleophiles, exhibiting rates that are even comparable to some charged nucleophiles, such as enolates [1, 2]. Most enamines, unfortunately, are sensitive to hydrolysis. The parent enamine, N, N-dimethylvinylamine, has in fact been prepared [3], but appears to be uns- ble. Enamines of cyclic ketones and many aldehydes can readily be isolated, however [4-7]. The instability of enamines might at first appear to diminish the utility of enamines as nucleophiles, but actually this property can be viewed as an added benefit: enamines can be readily and rapidly generated catalytically by using a suitable amine and a carbonyl compound. The condensation of aldehydes or ketones with amines initially affords an imine or iminium ion, which then rapidly loses a proton to afford the corresponding enamine (Scheme 1).

From the Back Cover:

Authoritative, broad overview of the field, compiled by 74 expertsCritical presentation of the best organocatalytic and related methodologies available today for practical asymmetric synthesisProvides alternative, greener syntheses with simple and easily used catalysts helping avoid the use of expensive and/or toxic metals

"Asymmetric Organocatalysis" is the first reference work giving an overview of this dynamic, young field that is rapidly gaining significance for economical and environmentally friendly organic synthesis. It comprehensively covers all the catalysts and reactions within the four distinct activation modes: Bronsted base catalysis, Bronsted acid catalysis, Lewis base catalysis and Lewis acid catalysis. Typical or general experimental procedures as well as mechanistic, technical and theoretical aspects are included, allowing the reader to clearly see how simple, clean and efficient this chemistry is.

This 2-volume set consists of:
Asymmetric Organocatalysis 1 Lewis Base and Acid Catalysts
Asymmetric Organocatalysis 2: Bronsted Base and Acid Catalysts, and Additional Topics

Both volumes are also available separately.

Further information about Asymmetric Organocatalysis (including sample pages and the table of contents)

General information about Science of Synthesis

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