Organic Letters
Organic Letters
5 years ago

Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls

Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls
Jeffrey S. Johnson, James Giarrusso, Dung T. Do
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01225

DOI: 10.1021/acs.orglett.7b01225

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