Department of Chemistry 232 Choppin Hall Louisiana State University Baton Rouge, Louisiana 70803, United States.
J Org Chem. 2017 Oct 6;82(19):10659-10664. doi: 10.1021/acs.joc.7b01687. Epub 2017 Sep 8.
Herein, we report an improved protocol for the concise synthesis of functionalized 1,4- and 1,6-dicarbonyl-derived monosilyl enol ethers via ionization of α'-hydroxy silyl enol ethers to generate unsymmetrical silyloxyallyl cations that were subsequently captured by TBS silyl enolates. These transformations were efficiently performed in acetonitrile at room temperature by employing pyridinium triflate as a catalyst. Our new reaction conditions are operationally more practical and broaden the accessibility of various 1,4- and 1,6-dicarbonyl groups, which include diketone, ketoester, and ketothioester functionalities.
在此，我们报告了一种改进的方法，通过α'-羟基硅基烯醇醚的电离来生成不对称的硅氧基烯丙基阳离子，然后用 TBS 硅基烯醇醚捕获，从而简洁地合成功能化的 1,4-和 1,6-二羰基衍生的单硅基烯醚。这些转化在室温下在乙腈中通过使用三氟甲磺酸吡啶盐作为催化剂有效地进行。我们的新反应条件在操作上更实用，并拓宽了各种 1,4-和 1,6-二羰基基团的可及性，包括二酮、酮酯和酮硫酯官能团。
