Design, synthesis and applications of new families of chiral sulfonic acids

Two new families of chiral arenesulfonic acids were synthesised in a short, robust and scalable synthetic sequence involving a key cross-coupling step of an aromatic scaffold with a suitable chiral auxiliary. The flexibility of the synthetic route and the ready availability of a range of naturally occurring chiral auxiliaries allowed us to prepare nine enantiomerically pure sulfonic acids with a tunable stereochemical environment. Application of the strong chiral Bronsted acids was demonstrated in an enantioselective nitrone/enol ether 1,3-dipolar cycloaddition.