Journal of the American Chemical Society p. 8212 - 8218 (1989)
Update date:2022-08-04
Topics:
Clennan, Edward L.
Chen, Xiangning
The reaction of singlet oxygen with a series of allylic sulfoxides, sulfones, and sulfides have been examined as a function of extent of reaction, temperature, and solvent.Hydroperoxy groups but not alkyl, hydrogen, or hydroxyl on chiral carbons β to sulfide sulfur induce diastereoselective sulfoxide formations.Evidence is presented that suggests that the oxidation at sulfur occurs with anchimeric assistance from the hydroperoxy group via a favorable sulfurane-like transition state.
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