Construction of 3-amino-2-oxindoles by direct amination of aniline or α-amino-acid derivatives to 3-bromooxindoles

Abstract

The asymmetric amination of anilines to 3-bromooxindoles was developed in the presence of a bis(oxazoline)-Ni(dppp)Cl2 complex, to provide enantiomerically enriched 3-amino-2-oxindoles with quaternary stereocenters in up to 90% yield with 92:8 er. Simultaneously, direct stereoselective amination of α-amino-acid methyl esters to 3-bromooxindoles was also accomplished without any catalysts, which furnished the 3-amino-2-oxindole derivatives in high yields with moderate diastereoselectivities.