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

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journal contribution
posted on 2015-06-19, 00:00 authored by Linqing Wang, Dongxu Yang, Dan Li, Rui Wang
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 (R)-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.