Novel spirocyclic scaffold accessed via tandem Claisen rearrangement – intramolecular Michael addition

• DOI: 10.3762/bxiv.2022.83.v1
• Publication Date: 2022-10-11T14:41:15Z
• Authors: Anastasia Vepreva; Alexander Yanovich; Dmitry Dar'in; Grigory Kantin; Alexander Bunev; Mikhail Krasavin

A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on Rh2(esp)2-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into O-H bond of phenols is described. The initial adducts underwent a thermally promoted Claisen rearrangement followed by DABCO-catalyzed intramolecular 5-exo-dig Michael addition.