Mechanism of the yeast mediated reduction of nitrostyrenes in light petroleum

Abstract

The yeast mediated reduction of a range of α- and β-deutero substituted nitrostyrenes has been conducted in light petroleum in the presence of a small amount of water or D₂O. NMR analysis of the products from these reactions has allowed the determination of the mechanism of this yeast reduction reaction. The results indicate that initially, a reversible non-stereoselective protonation occurs at the β-centre, followed by stereoselective addition of hydride at the α-position.