Catalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-Oxindoles


  • This research was supported by start-up funds from the University of California, Davis and a grant from the ACS-PRF (49I8I-DNI1). N.V.H. is a recipient of the Eugene Cota-Robles Graduate Fellowship.


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No more double trouble: The competing double-addition pathway was suppressed when chiral scandium(III) and indium(III) complexes were used to catalyze the addition of indoles and other π nucleophiles to N-alkylated and unprotected isatins (see picture). The resulting biologically relevant substituted 3-hydroxy-2-oxindoles were obtained in high yield with high enantioselectivity. Tf=trifluoromethanesulfonyl.