Beilstein J. Org. Chem.2024,20, 561–569, doi:10.3762/bjoc.20.48
(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 diazoarylidenesuccinimides (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: diazoarylidenesuccinimides; intramolecular cyclization; rhodium(II) carbene O–H insertion; spirocycles; Introduction
Spirocyclic motifs have emerged as auspicious frameworks for
towards spirocyclic scaffolds as a goal of great value [6][7][8][9].
A rich synthetic platform for the design of various types of spiroheterocycles is provided by cyclic diazo compounds [10]. Recently, we and others have demonstrated the efficient use of diazoarylidenesuccinimides (DAS, 1) in the
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Graphical Abstract
Scheme 1:
DAS spirocyclizations reported earlier and the synthetic methodology investigated in this work.