In an article, author is Srinivasulu, Vunnam, once mentioned the application of 90965-06-3, Name: Dimethyl (1-diazo-2-oxopropyl)phosphonate, Name is Dimethyl (1-diazo-2-oxopropyl)phosphonate, molecular formula is C5H9N2O4P, molecular weight is 192.1097, MDL number is MFCD07368360, category is chiral-nitrogen-ligands. Now introduce a scientific discovery about this category.
Divergent Strategy for Diastereocontrolled Synthesis of Small- and Medium-Ring Architectures
Nitrogen and oxygen medium rings, in particular nine-membered rings, epitomize a unique area of chemical space that occurs in many natural products and biologically appealing compounds. The scarcity of 8- to 12-membered rings among clinically approved drugs is indicative of the difficulties associated with their synthesis, principally owing to the unfavorable entropy and transannular strain. We report here a scandium triflate-catalyzed reaction that allows for a modular access to a diverse collection of nine-membered ring heterocycles in a one-pot cascade and with complete diastereocontrol. This cascade features an intramolecular addition of an acyl group-derived enol to a alpha,beta-unsaturated carbonyl moiety, leading to N- and O-derived medium-ring systems. Computational studies using the density functional theory support the proposed mechanism. Additionally, a one-pot cascade leading to hexacyclic chromeno[3′,4′:2,3]indolizino[8,7-b]indole architectures, with six fused rings and four contiguous chiral centers, is reported. This novel cascade features many concerted events, including the formation of two azomethine ylides, [3 +2]-cycloaddition, 1,3-sigmatropic rearrangement, Michael addition, and Pictet-Spengler reaction among others. Phenotypic screening of the resulting oxazonine collection identified chemical probes that regulate mitochondrial membrane potential, adenosine 5′-triphosphate contents, and reactive oxygen species levels in hepatoma cells (Hepa1-6), a promising approach for targeting cancer and metabolic disorders.
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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
,Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis