Synonyms:Samariumdiiodide; Samarium(II) iodide
99% *data from raw suppliers
Samarium(II)Iodide(0.1MinTHF) *data from reagent suppliers
There total 21 articles about SAMARIUM(II) IODIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
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The study presents a novel and efficient chiral auxiliary-based method for the synthesis of C-glycosylated amino acids. The key step involves a 1,3-dipolar cycloaddition of a chiral glycine equivalent and carbohydrate building blocks, leading to the formation of products with high regio- and diastereoselectivity. The chiral auxiliary, derived from (?)-menthone or (+)-menthone, allows for the synthesis of corresponding diastereomers. The method is designed to meet criteria for an easy and broadly applicable approach to a variety of products with different configurations, as well as orthogonal protecting group strategies. The study also explores the reductive cleavage of the N?O bond using SmI2, which is compatible with the protecting groups on the glycosidic moiety. The approach is demonstrated to be broadly applicable with various aglycosidic building blocks, and it is shown that a chiral glycine equivalent is necessary for the diastereomeric purity of the cycloaddition products. The research was financially supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.
The study by Scott T. Handy and Duncan Omune investigates the reductive cyclization of tethered bis-enones with one-carbon tethers, focusing on the influence of reaction conditions and α-substitution on the cyclization pathway. They found that the cyclization products, either pinacol or hydrodimerization-type, are highly dependent on these factors. The researchers synthesized three cyclization substrates and explored their reductive cyclization under electrochemical conditions and using samarium diiodide. They observed that electrochemical conditions favored pinacol-type products, while samarium diiodide favored reductive cyclization products. The study suggests that chelation and steric effects play a crucial role in determining the cyclization pathway, with Lewis acidic metals promoting pinacol formation and non-chelatable metals favoring reductive cyclization. This mechanistic understanding was further supported by experiments using magnesium in methanol, which resulted in pinacol products. The findings highlight the importance of reaction conditions in controlling the cyclization outcome and provide insights into the mechanism of reductive cyclization reactions.
The research focuses on the enantiospecific synthesis of a novel rearranged eunicellane diterpenoid using SmI2-mediated cyclization. The study investigates the synthesis and cyclization of α-geranylated carvones to assemble marine-derived diterpenoids. Key reactants include side-chain hydrogenated carvone, geraniol-derived aldehydes, and samarium diiodide (SmI2). The experiments involve 3-hydroxyalkylation, retro-aldol fragmentation, and NOESY-based structure analysis to reveal the presence of an ansa bridge across a twist-boat six-membered ring in the synthesized diterpenoid. Analytical techniques used in the study include NMR, IR, MS, UV/Vis spectroscopy, and X-ray crystallography to confirm the structures and properties of the synthesized compounds. The research provides insights into the assembly of eunicellane-type diterpenoids and introduces a novel skeletal structure, isoeunicellane, with potential for further structural variations.
The research explores a new reaction sequence involving the formation of R-aminoalkyl radicals, their addition to unactivated double bonds, reduction to carbanions, and subsequent trapping by electrophiles to synthesize pyrrolidines with functional groups at C-3. The study highlights the significance of constructing carbon-carbon bonds adjacent to nitrogen for synthesizing biologically important nitrogen-containing compounds. Key chemicals involved in this research include N-(R-aminobutyl)benzotriazole, which is prepared from the condensation of a secondary amine, butyraldehyde, and benzotriazole. This compound serves as the precursor for the radical intermediates. SmI2 (samarium diiodide) plays a crucial role in the reduction steps, facilitating the transformation of radicals to carbanions. Various electrophiles such as water, methyl alcohol-d, ketones, aldehydes, iodine, and isopropyl isocyanate are used to trap the carbanions, yielding different pyrrolidine derivatives. The research demonstrates the potential of this novel tandem cyclization strategy for the synthesis of alkaloids and other nitrogen-containing heterocycles.
The study investigates the acid-induced and reductive transformations of enantiopure 3,6-dihydro-2H-1,2-oxazines, which are carbohydrate-derived heterocycles. These oxazines, synthesized from lithiated alkoxyallenes and chiral carbohydrate-derived nitrones via a [3+3] cyclization, serve as versatile intermediates for creating various target compounds. Acid-catalyzed transformations of these oxazines yield enantiopure furano-1,2-oxazines or pyrano-1,2-oxazines, with reaction conditions dictating the degree of solvolysis. The N–O bond of these oxazines can be reductively cleaved using hydrogen/palladium or samarium diiodide, resulting in enantiopure aminofuran and aminopyran derivatives. These derivatives are essentially protected 4-amino-1,4-dideoxyhex-3-ulose or 4-amino-1,4-dideoxyoct-3-ulose derivatives, representing a short and stereocontrolled route to amino carbohydrate derivatives. The study also includes X-ray analysis of certain products to confirm their structures and investigate hydrogen bonding networks.
Kamar Sahloul, Linhao Sun, Alexandre Requet, Youhana Chahine, and Mohamed Mellah present an innovative electrochemical method for the in situ preparation of samarium diiodide (SmI2) in tetrahydrofuran (THF) by directly oxidizing a samarium metallic rod. This method allows for the continuous production of SmI2, overcoming the limitations of traditional synthesis methods that require large amounts of solvents and strictly inert atmospheres. The electrogenerated SmI2 was characterized by electrochemistry and UV/Vis spectroscopy, confirming its formation and reactivity. The study demonstrates the application of this SmI2 in various organic reactions, including homocoupling of aldehydes and ketones, reductive coupling of imines, and Barbier-type reactions, achieving good to excellent yields and significant solvent savings compared to classical procedures. This work highlights the potential of electrochemistry for the synthesis of sensitive lanthanide reagents and offers a more efficient and sustainable approach to organic synthesis using SmI2.
The study investigates the aminolysis of aziridines catalyzed by samarium diiodide and samarium iodobinaphtholate. Aziridines, which are three-membered heterocyclic compounds with a nitrogen atom, are reacted with aromatic amines to produce 1,2-diamines, which are important scaffolds for biologically active molecules and used in enantioselective catalysis. The researchers found that samarium diiodide efficiently catalyzes the ring-opening of both activated and non-activated aziridines, leading to the formation of various N-diprotected ?-diamines. The study also compared the effectiveness of different N-protecting groups on aziridines, with N-Boc (t-butoxycarbonyl) protection yielding the best results. Additionally, samarium iodobinaphtholate was tested for enantioselective aminolysis of aziridines, showing total conversion but low enantioselectivities, with encouraging results observed for N-Boc aziridines. The reactions were optimized in terms of solvent (THF or DCE) and reaction conditions, with microwave irradiation significantly reducing reaction times.
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