Diastereoselective aldol-type interception of phenolic oxonium ylides for the direct assembly of 2,2-disubstituted dihydrobenzofurans

Abstract

A Rh₂(OAc)₄ catalyzed intermolecular aldol-type interception of phenolic oxonium ylides with isatins has been developed, which provides an effective access to 2,2-disubstituted dihydrobenzofuran derivatives containing 3-hydroxyoxindole in high yields and with high diastereoselectivities under mild reaction conditions. The antiproliferation activity of these synthesized dihydrobenzofuran and 3-hydroxyoxindole hybrid products has been tested via the CCK8 assay in different cancer cell lines; compounds 3s and 3t exhibit good anticancer potency against human colon cancer cells (HCT116 cells, 3s: IC₅₀ = 15.99 μM; 3t: IC₅₀ = 14.48 μM) compared to other tested compounds.