Optically active 4-substituted cis-1,2-diphenylethylene oxides and related 1,2-diphenylethane diols

Abstract

Erythro 1-(4′-chlorophenyl)- and 1-(4′-methylphenyl)-2-phenylethane diols with [1 S:2 R] and [1 R:2 S] absolute stereochemistry were synthesized and converted to the corresponding 4′-substituted [1 S:2 R] and [1 R:2 S] cis-stilbene oxides by the following sequence: formation of 2-methoxydioxalanes, conversion to halohydrins and cyclization to cis epoxides. Substantial amounts of optically active 4′-substituted trans-stilbene oxides were also produced. The enzyme epoxide hydrase stereoselectivity adds water at the [ S] carbon atom of the cis-stilbene oxides with inversion of configuration to produce [ R: R] diols. Facile enzymatic resolution of cis - 1 - (4′ - nitrophenyl) - 2 - phenylethylene oxide was achieved. Optical properties, including CD spectra of the above compounds are described.