通过用氧鎓盐氧化二酮来获得亲二烯体烯三酮合成子。
Access to dienophilic ene-triketone synthons by oxidation of diketones with an oxoammonium salt.
机构信息
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269, USA.
出版信息
Org Lett. 2012 Jan 20;14(2):498-501. doi: 10.1021/ol2030873. Epub 2011 Dec 29.
Abstract
Here we describe the oxidation of 1,3-cyclohexanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt's salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diels-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex molecules.
摘要
在这里，我们描述了用 4-乙酰氨基-2,2,6,6-四甲基哌啶-1-氧代铵四氟硼酸盐（Bobbitt 盐）氧化 1,3-环己二酮生成 5-烯-1,2,4-三酮，产率中等至良好（40-80%）。这种廉价的氧化剂促进了氧化和消除的级联反应，生成了新型的烯三酮。这些产物的反应性在 Diels-Alder 反应中得到了探索，并提供了中等至良好收率的环加成产物。本研究中描述的产物代表了独特的、多官能化和多功能的构建块，可用于合成更复杂的分子。
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