Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls
- Resource Type
- Authors
- James Giarrusso; Dung T. Do; Jeffrey S. Johnson
- Source
- Organic Letters. 19:3107-3110
- Subject
- 010405 organic chemistry
Chemistry
Organic Chemistry
Ionic bonding
Elemental oxygen
Raw material
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
Catalysis
Hydrogenolysis
Site selective
Organic chemistry
Physical and Theoretical Chemistry
Stoichiometry
- Language
- ISSN
- 1523-7052
1523-7060
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.