Homoallylically Controlled Epoxidation of Δ4-Cis-1,2-Disubstituted Cyclohexenes
Stereochemical control during the epoxidation of cis-1-[N-Cbz]-2-[hydroxymethyl]-cyclohex-4-enes with MCPBA is dependent on hydroxyl functionalization which apparently determines ring conformation. Unprotected or acetate-derivatized compounds afford exclusively syn epoxide products. Silyl ether protected analogs furnish predominantly products derived from anti delivery of oxygen. Respective 2-carbomethoxy and benzyl carbamate-protected aminomethyl derivatives show stereospecificity similar to the free hydroxyl and acetate-protected substrates.
Montclair State University Digital Commons Citation
Rotella, David, "Homoallylically Controlled Epoxidation of Δ4-Cis-1,2-Disubstituted Cyclohexenes" (1989). Department of Chemistry and Biochemistry Faculty Scholarship and Creative Works. 286.