Wonilowicz Laura G, Mehta Milauni M, Kamecke Lisa L, French Sarah A, Garg Neil K
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Org Lett. 2024 Aug 2;26(30):6465-6470. doi: 10.1021/acs.orglett.4c02294. Epub 2024 Jul 24.
Reactions of α-pyrones with oxacyclic allenes in Diels-Alder trappings are described. We investigate regioselectivity trends and perform competition experiments to assess the influence of structural and electronic features on relative reaction rates. We also demonstrate the stereospecific trapping of an oxacyclic allene, which proceeds in high optical yield. This study provides insight into strained cyclic allene reactivity, as well as new synthetic tools for the rapid construction of complex, heterocyclic scaffolds.
描述了α-吡喃酮与氧杂环丙二烯在狄尔斯-阿尔德捕获反应中的反应。我们研究区域选择性趋势，并进行竞争实验以评估结构和电子特征对相对反应速率的影响。我们还证明了氧杂环丙二烯的立体选择性捕获，其以高光学产率进行。这项研究深入了解了应变环状丙二烯的反应性，以及用于快速构建复杂杂环骨架的新合成工具。
