35106-82-2Relevant articles and documents
Diastereoselective Synthesis of the ABCD Ring System of Rubriflordilactone B
Roth, Hudson G.,Nicewicz, David A.
, p. 48 - 51 (2021/11/09)
A novel nine-step diastereoselective route to the ABCD ring system of the natural product rubriflordilactone B is reported. Use of an α-substituted butenolide derived from maleic anhydride facilitated a 1,4-conjugate addition to provide a diene. The order in which a ringclosing metathesis and enolate oxidation were performed on this compound dictated the relative stereochemistry of the target. The final product exhibited anisotropic effects during roomerature NMR studies, requiring elevatederature experiments to confirm its identity.
Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons
Hemric, Brett N.,Chen, Andy W.,Wang, Qiu
, p. 1468 - 1488 (2019/01/25)
Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.
Stable Zero-Valent Nickel Nanoparticles in Glycerol: Synthesis and Applications in Selective Hydrogenations
Reina, Antonio,Favier, Isabelle,Pradel, Christian,Gómez, Montserrat
supporting information, p. 3544 - 3552 (2018/08/01)
Small (mean diameter, ca. 1.2 nm) and well-dispersed zero-valent nickel nanoparticles (NiNPs) stabilized by cinchona-based alkaloids and TPPTS (tris(3-sulfophenyl)phosphine trisodium salt), were synthesized from the organometallic precursor [Ni(cod)2] in neat glycerol under hydrogen pressure. NiNPs were fully characterized ((HR)-TEM, EDX, XPS, XRD, IR, magnetization), both at solid state and directly from the corresponding colloidal solutions in glycerol due to its negligible vapour pressure. NiNPs dispersed in glycerol were applied in hydrogenation reactions, in particular in semihydrogenation of alkynes to give (Z)-alkenes under satisfactory conditions (3 bar H2, 1 mol% Ni, 100 °C), showing remarkable activity and selectivity. The catalytic phase was recycled at least ten times without loss of activity, affording in each case metal-free organic products. Other functional groups such as nitro, nitrile and formyl groups were efficiently hydrogenated to the corresponding anilines, benzylamines and benzylalcohols respectively (77–95% yields). (Figure presented.).
