Homoallylically controlled epoxidation of Δ4-cis-1,2-disubstituted cyclohexenes

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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.

Original languageEnglish
Pages (from-to)1913-1916
Number of pages4
JournalTetrahedron Letters
Issue number15
StatePublished - 1989


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