Asymmetric Organocatalysis

Language: English

Published by Springer, 2012

3642262791 / 9783642262791

Series: Book 4 of 84 - Topics in Current Chemistry

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Druck auf Anfrage Neuware - Printed after ordering - 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).…

Seller Inventory # 9783642262791

Title
Asymmetric Organocatalysis
Author
Benjamin List
Publisher
Springer
Publication year
2012
Condition
Neu
Binding
Taschenbuch
Language
English
ISBN 10
3642262791
ISBN 13
9783642262791
Item weight
709 grams
Dimensions
235x155x26 mm
Series
Book 4 of 84: Topics in Current Chemistry

AHA-BUCH GmbH

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