Asymmetric Catalytic Concise Synthesis of Hetero-3,3 '-Bisoxindoles for the Construction of Bispyrroloindoline Alkaloids

Asymmetric nucleophilic addition of 3-substituted N-Boc oxindoles to 3-bromooxindoles was designed to directly construct hetero-3,3'-bisoxindoles, with varying vicinal quaternary carbon stereocenters and N-substituents. The reaction progressed efficiently with high yields, good diastereo- and enantioselectivity (up to >99% ee) under mild reaction conditions catalyzed by chiral N,N'-dioxide/metal complexes. This methodology enabled the facile transformation of the generated hetero-3,3'-bisoxindoles into diverse hexahydropyrroloindole alkaloids with potential antiparasitic and anticancer properties.

Automated summary

This study presents a method for the direct synthesis of hetero-3,3'-bisoxindoles with varying vicinal quaternary carbon stereocenters and N-substituents. The reaction proceeds efficiently with high yields, good selectivity, and the generated products can be easily transformed into diverse hexahydropyrroloindole alkaloids with potential antiparasitic and anticancer properties.