1353094-23-1Relevant academic research and scientific papers
Access to dienophilic ene-triketone synthons by oxidation of diketones with an oxoammonium salt
Eddy, Nicholas A.,Kelly, Christopher B.,Mercadante, Michael A.,Leadbeater, Nicholas E.,Fenteany, Gabriel
supporting information; experimental part, p. 498 - 501 (2012/02/16)
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.
