Influence of chiral thiols on the diastereoselective synthesis of γ-lactams from cyclic anhydrides

The synthesis of γ-lactams from both four-component and imine-anhydride reactions is reported. The synthesis of 2-phenylcyclohexanethiol is described and this compound was evaluated along with an additional seven chiral thiols. A range of selectivity and yields was observed and comparisons to established reactions are made in order to account for the observed reactivity.