Department of Chemistry , Indian Institute of Technology Hyderabad , Kandi, Sangareddy , Telangana 502 285 , India.
J Org Chem. 2019 Nov 1;84(21):14270-14280. doi: 10.1021/acs.joc.9b02064. Epub 2019 Oct 7.
Herein, we report a one-pot Lewis acid mediated synthesis of bi- and triarylpropanal derivatives and their corresponding isomeric ketones from aromatic enol ethers. This transformation takes place via nucleophilic attack of enol ethers to electron-rich benzyl alcohols. The substrate scope of this indicates that it might proceed via quinomethoxy methide as a key intermediate leading to propanal derivatives, and their Wagner-Meerwein rearrangement afforded isomeric ketones. Further, this methodology was applied for the synthesis of (±)-tetrahydronyasol, propterol A, and 1,3-diarylpropane.
在此，我们报告了一种一锅 Lewis 酸介导的合成双芳基和三芳基丙醛衍生物及其相应的异构酮的方法，该方法是通过烯醇醚对富电子苄醇的亲核进攻来实现的。该反应底物范围表明，它可能通过醌甲氧基甲叉作为关键中间体生成丙醛衍生物，其 Wagner-Meerwein 重排得到异构酮。此外，该方法还用于（±）-四氢尼亚醇、普罗特醇 A 和 1,3-二芳基丙烷的合成。
