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Updated: May 30, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
09:27

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues

Published on: February 17, 2017

β-シロキシ-α-ハロアルデヒドの急速な1ポット合成

Jakub Saadi1, Matsujiro Akakura, Hisashi Yamamoto

  • 1Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.

Journal of the American Chemical Society
|August 6, 2011
PubMed
まとめ

研究者らは,ハロゲン化アセタルデヒド誘導体を用いた新しいムカイヤマクロスアルドール反応を開発した. この方法は,精密なステレオ化学的制御で複雑なポリケチド断片を効率的に作成します.

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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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