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Asymmetric Organocatalysis(Topics in Current Chemistry Vol.291) P XII, 460 p. '09

List, Benjamin  編
在庫状況 海外在庫有り  お届け予定日 1ヶ月  数量 冊 
価格 \69,109(税込)         

発行年月 2012年05月
出版社/提供元
出版国 ドイツ
言語 英語
媒体 冊子
装丁 paper
ページ数/巻数 XII, 460 p.
ジャンル 洋書/理工学/化学/有機化学
ISBN 9783642262791
商品コード 1010183503
本の性格 学術書
商品URL
参照
https://kw.maruzen.co.jp/ims/itemDetail.html?itmCd=1010183503

著者紹介

List, Benjamin(編者):Winner of the Nobel Prize in Chemistry 2021

内容

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).

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