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通过 Ag(I)-或 Ag(I)-Au(I)-催化的炔丙醇和α-酮酯的级联环化反应合成呋喃并[2,3-b]吡喃-2-酮。

Synthesis of Furo[2,3-b]pyran-2-ones through Ag(I)- or Ag(I)-Au(I)-Catalyzed Cascade Annulation of Alkynols and α-Ketoesters.

机构信息

Division of Organic Chemistry, CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road, Pune-411008, India.

Academy of Scientific and Innovative Research (AcSIR), New Delhi, India.

出版信息

Org Lett. 2018 Feb 2;20(3):872-875. doi: 10.1021/acs.orglett.7b04027. Epub 2018 Jan 22.

DOI:10.1021/acs.orglett.7b04027
PMID:29356552
Abstract

Ag(I)- or Ag(I)-Au(I)-catalyzed cascade annulation of alkynols (5-hexyn-1-ol systems) with α-ketoesters involving a dual activation process (π and σ) has been developed for the first time. This reaction proceeds through cycloisomerization of alkynol to give the 6-endo-enol ether followed by annulation with an α-ketoester to furnish furo[2,3-b]pyran-2-ones in good yields. Chemical structures of all products were rigorously confirmed by single crystal X-ray analysis and analogy.

摘要

Ag(I)-或 Ag(I)-Au(I)-催化的炔丙醇(5-己炔-1-醇体系)与α-酮酸酯的级联环化反应,涉及双活化过程(π 和 σ),这是首次被开发出来的。该反应通过炔丙醇的环异构化生成 6-endo-烯醇醚,然后与α-酮酸酯环化,以高产率得到呋喃[2,3-b]吡喃-2-酮。所有产物的化学结构都通过单晶 X 射线分析和类推得到了严格的证实。

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