Catalytic Enantioselective Ring-Opening and Ring-Closing Reactions of 3‑Isothiocyanato Oxindoles and <i>N</i>‑(2-Picolinoyl)aziridines

Abstract

3-Isothiocyanato oxindoles have been successfully applied to an asymmetric formal [3 + 3] cycloaddition reaction with aziridines for the first time. The reaction was efficiently mediated by an in situ generated magnesium catalyst employing (<i>R</i>)-3,3′-fluorous-BINOL as a simple chiral ligand. Serials of polycyclic frameworks could be obtained after a ring-closing step. The enantioenriched ring-opening product was also utilized to modified amino acids, peptides, and bifunctional organocatalyst