Chiral BOX-Cu(OTf)2 catalyzed enantioselective aminolactonization of the tert-butyl ester of alkenoic acids has been developed via in situ aziridination using PhINNs as the nitrene source. It provides exclusively trans-γ- and δ-amino lactones including an additional all-carbon quaternary stereo-centre with up to 98% ee in good to excellent yields.

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A one-pot asymmetric aminoarylation reaction has been executed for the synthesis of trans-4-amino-5-aryltetrahydrobenzo[c]azepines with excellent diastereo- and enantioselectivity (dr: >99: 1 and ee up to 97%). The reaction progressed via aziridination of prochiral N-tosyl-N-cinnamyl benzylamines followed by intramolecular 7-endo-tet Friedel-Crafts cyclization of the in situ generated tethered aziridines, where the combination of Cu(OTf)2 catalyst and PhINNs as a nitrene source were found to be effective. Chiral indenyl bis(oxazoline) was testified to be an efficient ligand for the catalytic enantioselective version of this one-pot transformation. This 7-endo-tet cyclization is in contrast with the Baldwin cyclization rule.