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

CCS Chemistry
2021.0

Abstract

Asymmetric nucleophilic addition of 3-substituted NBoc 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. © 2021 Chinese Chemical Society. All right reserved.

DOI： 10.31635/ccschem.020.202000443

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