Entry to new spiro heterocycles via tandem Rh(II)-catalyzed O–H insertion – base-promoted cyclization involving diazo arylidene succinimides

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

Beilstein Arch. 2023, 202350. https://doi.org/10.3762/bxiv.2023.50.v1

Published 21 Nov 2023

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A facile approach to novel medicinally relevant spiro heterocyclic scaffolds (namely furan-2(5H)-ones, tetrahydrofurans and pyrans spiro-conjugated with the succinimide ring) has been developed. The protocol consists of Rh(II)-catalyzed insertion of heterocyclic carbenes derived from diazo arylidene succinimides (DAS) into the O-H bond of propiolic/allenic acids or brominated alcohols, followed by base-promoted cyclization to afford the target spirocyclic compounds in good to high yields.

Keywords: rhodium(II) carbene O-H insertion; diazo arylidene succinimides; intramolecular cyclization; spirocycles

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Yanovich, A.; Vepreva, A.; Malkova, K.; Kantin, G.; Dar'in, D. Beilstein Arch. 2023, 202350. doi:10.3762/bxiv.2023.50.v1

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