Title

Homoallylically Controlled Epoxidation of Δ4-Cis-1,2-Disubstituted Cyclohexenes

Document Type

Article

Publication Date

1-1-1989

Abstract

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.

DOI

10.1016/S0040-4039(00)99612-6

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