Stereospecific oxygen rearrangement in the reduction of optically pure methyl mandelate to phenylethanol isomers

Abstract

The reduction of methyl (S)-(+)-mandelate, 1, produces the expected 2-phenylethanol, 3, and the unexpected optically pure 1-phenylethanol, 6, by a stereospecific oxygen atom metathesis; which occurs through a styrene oxide intermediate, whose concentration varies with solvent polarity.