Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls
The diastereoconvergent synthesis of spirocyclic endoperoxides using a Meldrum's acid scaffold has been accomplished by employing readily available feedstock chemicals. Site selective C-H oxidation of the bis(β-dicarbonyl) substrates was performed using elemental oxygen as the stoichiometric oxidant and a commercial Cu(II) catalyst. Sequential hydrogenolysis and ionic reduction of these endoperoxides provided fully substituted tetrahydrofurans in high yields and diastereoselectivity.
Electrophilicity parameters of 5-benzylidene-2,2-dimethyl[1,3]dioxane-4,6- diones (benzylidene meldrum's acids)
(Chemical Equation Presented) Kinetics of the reactions of four benzylidene Meldrum's acids 1 with acceptor-substituted carbanions 2 were studied photometrically in DMSO at 20°C. The reactions follow second-order kinetics, and the second-order rate consta
Kaumanns, Oliver,Mayr, Herbert
p. 2738 - 2745
(2008/09/20)
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