Enantioselectivity in a free-radical oxidation: measurement of small enantiomeric excesses

Abstract

Partial conversion of 2-methyl-1-phenylpropan-1-ol into isobutyrophenone by the acyl aminoxyl radicals formed on oxidation of enantiomerically pure N-fenchelylbenzohydroxamic acid or its para-nitro derivative occurs with small but measurable enantioselectivity. This has been demonstrated using HPLC with diode-laser-based polarimetric detection to examine unchanged alcohol in the reaction mixtures.