Retrosynthetic Analysis of α-Alkenyl-β-Diketones: Regio- and Stereoselective Two-Step Synthesis of Highly Arylated Representatives from Acetylenes, Ketones, and Acyl Chlorides.,The Journal of Organic Chemistry

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Retrosynthetic Analysis of α-Alkenyl-β-Diketones: Regio- and Stereoselective Two-Step Synthesis of Highly Arylated Representatives from Acetylenes, Ketones, and Acyl Chlorides.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-06-03 , DOI: 10.1021/acs.joc.0c00768
Dmitrii A Shabalin ₁ , Elena V Ivanova ₁ , Igor' A Ushakov ₁ , Elena Yu Schmidt ₁ , Boris A Trofimov ₁

Affiliation

Highly arylated α-alkenyl-β-diketones are synthesized via a two-step sequence consisting of (i) potassium tert-butoxide/DMSO-catalyzed (E)-stereoselective C–H functionalization of ketones with acetylenes followed by (ii) magnesium bromide etherate/DIPEA-soft enolization of the formed β,γ-unsaturated ketones and regioselective acylation with acyl chlorides. The method is compatible with a broad range of substrates and shown to be applicable as an intermediate stage in the construction of polyarylated heterocycles.

中文翻译：

α-链烯基-β-二酮的逆合成分析：乙炔基，酮和酰氯的高度丙烯酸化的区域和立体选择性两步合成法。

高度芳基化的α-烯基-β-二酮是通过两步序列合成的：（i）叔丁醇钾/ DMSO催化的乙炔经酮的（E）立体选择性CH官能化，然后是（ii）溴化镁生成的β，γ-不饱和酮的醚化/ DIPEA软化烯化反应，并用酰氯进行区域选择性酰化。该方法与广泛的底物相容，并且显示出可作为构建聚芳基杂环的中间阶段。

更新日期：2020-07-02

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