Asymmetric epoxy cyclohexenyl sulfones: readily accessible progenitors of stereo defined six-carbon arrays.
[formula: see text] Enantiopure epoxy vinyl sulfones serve as highly effective substrates for a variety of stereo- and regiospecific oxidation and nucleophilic functionalization reactions. These materials can be easily transformed to cyclic and acyclic six-carbon segments. Nucleophilic epoxidation of 3a,b followed by palladium[0] catalysis enables access to differentially protected arene diols 21 and 22.
Hentemann
M
M
Department of Chemistry, Purdue University West Lafayette, Indiana 47907, USA.
Fuchs
P L
PL
D004852:Epoxy Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D004852:Epoxy Compounds; D013450:Sulfones