N-Boc- α -diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N – H insertion reaction

Abstract
A technique has been proposed for incorporating a heterocyclic component into a glutarimide framework employing a Rh2(esp)2-catalyzed N–H insertion with the involvement of N-Boc-α-diazo glutarimide. The new diazo reagent is more stable, soluble and convenient to prepare than the previously suggested one. The approach permits the application of diverse heterocycles, including both aromatic and saturated NH-substrates. This yields structures that are appealing for generating cereblon ubiquitin-ligase ligands and for potential use in crafting PROTAC molecules.

Beilstein J. Org. Chem. 2023, 19, 1841–1848. doi:10.3762/bjoc.19.136

Source: Beilstein Journal of Organic Chemistry - December 7, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: CRBN ligands diazocarbonyl compounds – H insertion reaction N-heterocycles Rh(II)-catalysis Full Research Paper Source Type: research