Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.
J Org Chem. 2022 Sep 16;87(18):12175-12181. doi: 10.1021/acs.joc.2c01322. Epub 2022 Aug 25.
Polysubstituted allenes are useful synthetic intermediates in many applications, offering structural complexity, modularity, and their axial chirality in further transformations. While acyl and alkoxy-substituted allenes are known, there are currently few examples of allenes containing both functionalities and no reports of geminally substituted acyl/alkoxy allenes being isolated and characterized. Herein, we report the synthesis of tetrasubstituted allenes featuring a novel geminal acyl/alkoxy substitution. These unique "push-pull" allenes are bench-stable and exhibit interesting reactivity in several applications.
多取代丙二烯是许多应用中有用的合成中间体，提供结构复杂性、模块性和其在进一步转化中的轴手性。虽然已知酰基和烷氧基取代的丙二烯，但目前含有这两种官能团的丙二烯的例子很少，也没有关于偕二取代的酰基/烷氧基丙二烯被分离和表征的报道。在此，我们报告了具有新颖偕二酰基/烷氧基取代的四取代丙二烯的合成。这些独特的“推-拉”丙二烯在几种应用中具有良好的稳定性和有趣的反应性。
