Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O – H insertion/base-promoted cyclization involving diazoarylidene succinimides

Abstract
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 diazoarylidene 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.

Beilstein J. Org. Chem. 2024, 20, 561–569. doi:10.3762/bjoc.20.48

Source: Beilstein Journal of Organic Chemistry - March 11, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: diazoarylidene succinimides intramolecular cyclization rhodium(II) carbene O – H insertion spirocycles Full Research Paper Source Type: research