Beilstein J. Org. Chem.2023,19, 1841–1848, doi:10.3762/bjoc.19.136
, 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.
Keywords: CRBN ligands; diazocarbonyl compounds; N–Hinsertionreaction; N-heterocycles; Rh(II)-catalysis
)-catalyzed N–H-insertionreaction.
Preparation of diazo reagent 5.
Scope of NH insertion reaction of N-Boc-α-diazo glutarimide and various N-heterocycles. aIsolated yield; reaction scale ‒ 0.33 mmol of NH-heterocycle, 0.4 mmol of diazo reagent 5, catalyst ‒ 2.5 mM Rh2(esp)2 in DCM, 100‒300 μL (0.06‒0.18 mol
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Graphical Abstract
Figure 1:
Glutarimide-based immunomodulatory drugs (IMiDs) and CRBN ligands.
Beilstein J. Org. Chem.2012,8, 1499–1504, doi:10.3762/bjoc.8.169
migration of the N-acyl glycine derivatives [18]. The other consists of C–N bond-forming reactions, such as (c) a rhodium-catalyzed N–Hinsertionreaction with α-diazo-β-keto esters [19][20][21], and (d) α-oxidation of β-keto esters to the corresponding oximes and the subsequent hydrogenation [22]. However
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Graphical Abstract
Figure 1:
Synthetic methods for α-amino-β-keto esters.