N-t-butanesulfinyl amide: An optimised and versatile access from readily available starting materials

We report the synthesis of t-butanesulfinylphthalimide and its complete regioselective ring opening by a range of nucleophiles. Further treatment of the obtained N-t-butanesulfinyl amides under basic conditions has been shown to give t-butanesulfinamide. Although the involvement of chiral nucleophiles in this process did not allow the isolation of enantiomerically pure t-butanesulfinamide, we have accessed in a rapid and efficient fashion the original compounds bearing two H-bond sites and two chiral centers that shall potentially exhibit some organocatalytic activity by comparison with known structurally related compounds.