Access to dienophilic ene-triketone synthons by oxidation of diketones with an oxoammonium salt.
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.
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269, USA.
Nicholas A
NA
Eddy
Christopher B
CB
Kelly
Michael A
MA
Mercadante
Nicholas E
NE
Leadbeater
Gabriel
G
Fenteany
D003517:Cyclopentanes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D003517:Cyclopentanes; D007659:Ketones; D000644:Quaternary Ammonium Compounds