アルファ,ベータ不飽和ケトンに高度なエナンチオセレクティブの結合添加物, (塩) アル複合体によって触媒化された

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Updated: Jul 14, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Mark S Taylor1, David N Zalatan, Andreas M Lerchner

  • 1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Journal of the American Chemical Society
|January 27, 2005
PubMed
まとめ

キラルアルミニウム複合体は,エナチオセレクティブ結合添加反応を効率的に触媒化する. この方法は,複雑な分子を合成するのに有用な,多様なケトンから貴重なキラル構成要素を作成します.

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Base-Catalyzed Aldol Addition Reaction

As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation01:14

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

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Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

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Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

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Aldol Condensation with β-Diesters: Knoevenagel Condensation

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Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...