Output details

Mechanistic insights into transition metal-catalysed oxidation of a hydroxamic acid with in situ Diels-Alder trapping of the acyl nitroso derivative

Hetro-Diels Alder cycloaddition reactions provide a powerful synthetic tool in natural product based drug design. Many of these natural products contain multiple chiral centres; therefore catalysts used during synthesis must be highly specific to achieve asymmetric synthesis. The purpose of this research was to understand the behaviour of certain transition metal catalysts through detailed mechanistic studies. Because of the complexity of the task a number of techniques were employed including reaction kinetics, NMR spectroscopy, cyclic voltammetry and X-ray crystallography. The results showed that whilst one catalyst was sufficient to perform the oxidation, a second moiety was required to induce asymmetry.