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

Submitting author affiliation:
Saint Petersburg State University, Peterhof, Russian Federation

Beilstein Arch. 2022, 202283.

Published 11 Oct 2022

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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.

Keywords: rhodium(II) carbene O-H insertion; diazo arylidene succinimides; Claisen rearrangement; intramolecular Michael addition; spirocycles

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Vepreva, A.; Yanovich, A.; Dar'in, D.; Kantin, G.; Bunev, A.; Krasavin, M. Beilstein Arch. 2022, 202283. doi:10.3762/bxiv.2022.83.v1

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