Deconstructing α-Amidoalkyl Sulfones as Dual <i>d</i>-Sulfonyl/<i>a</i>-Azomethine Synthons: Synthesis of 3-Sulfonylmethylindole Aminals.

ABSTRACT: α-Amido sulfones (1) are widely applied as electrophilic aminoalkylation reagents. However, nonproductive sulfinate species are formed alongside. Here, we report that ethyl propiolate-promoted coupling of 1 and gramines provides 3-sulfonylmethylindole aminals II smoothly, thus establishing α-amido sulfones as dual donor/acceptor reagents with full atom incorporation on the target molecule. Simple adjustment of reactants loading allows one to revert the reaction outcome, leading to exclusive formation of 3-sulfonylmethylindoles I instead.

SUBMITTER: Dominguez G 

PROVIDER: S-EPMC12381929 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature