Refernces
10.1039/b717318k
The research presents a novel and general method for direct and highly stereoselective Ti-mediated Mannich reactions between simple esters and mixtures of oxime ethers, which are more stable and easier to prepare than traditional imines. The study focuses on the reaction of three types of esters with both aliphatic and aromatic oxime ethers, yielding b-amino carbonyl compounds and b-lactams with high syn-selectivity. The experiments utilized TiCl4–sBu2NH as a reagent and involved various esters and O-methyloximes, with the stereochemistry of the oxime ethers playing a crucial role in the reaction's outcome. The analysis of the products was conducted using 1H NMR spectroscopy to determine the syn/anti selectivity of the Mannich reaction products. The research also explored alternative reductive Ti-Mannich reactions using a TiCl4–PPh3 reagent, successfully synthesizing a variety of 3-(methoxyamino)-2-substituted esters with controlled stereochemistry.
10.1039/c9nj00030e
The study presents an efficient [3+2] cycloaddition reaction between nitrones and carbodiimides, leading to the synthesis of 1,2,4-oxadiazolidines. This reaction is characterized by high regioselectivity, mild and metal-free conditions, excellent functional group compatibility, and a broad substrate scope. The purpose of the chemicals used in the study was to explore and develop a method for synthesizing heterocyclic oxadiazolidines, which are potentially bio-active compounds. Nitrones, with various substituents on their aromatic or heteroaromatic rings, and carbodiimides, with different electron-donating or electron-withdrawing groups on their aromatic rings, were utilized to demonstrate the versatility and selectivity of the reaction. The study aimed to provide an efficient approach for the synthesis of heterocyclic compounds, contributing to the field of synthetic organic chemistry.
10.1016/S0040-4039(02)02336-5
The research focuses on the synthesis of a new nitrone derived from C2 symmetric piperidine, which is used for the creation of hydroxylated indolizidinones. The purpose of this study was to develop an alternative synthetic pathway to these biologically active molecules, which are known as glycosidase inhibitors. The researchers achieved this by oxidizing a C2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, using C-phenyl-N-phenylsulfonyloxaziridine. The resulting nitrone was too unstable for isolation and was therefore reacted in situ with dimethyl maleate, yielding a major adduct that was transformed into a protected dihydroxyindolizidinone. The conclusions of the research indicate that the synthetic process starting from a C2 symmetric piperidine can be considered an alternative method for synthesizing indolizidinones with a precise substitution pattern on the six-membered ring, despite the limited stability of the nitrone. Key chemicals used in this process include C-phenyl-N-phenylsulfonyloxaziridine, dimethyl maleate, and various reagents for the protection and oxidation steps.
10.1246/cl.1985.1049
The research focuses on the regioselective cycloaddition reactions of allylsilanes and silyl enol ethers with nitrones and nitrile oxides, aiming to synthesize homoallylamines. The study demonstrates that these nucleophilic reagents react regioselectively with 1,3-dipolar reagents to form isoxazolidines and isoxazolines, rather than undergoing 1,3-conjugate addition reactions. The process involves the use of allyltrimethylsilane, silyl enol ether, nitrones, and nitrile oxides. The cycloadducts derived from allylsilanes can be further converted to homoallylamines through hydrogenative cleavage of the nitrogen-oxygen bond, providing a new route for synthesizing these compounds, which are important precursors to heterocyclic compounds in organic synthesis. In contrast, cyanosilane reacts with nitrones in a 1,3-conjugate addition manner, yielding silyl ether of N-cyanomethylhydroxylamine. The research concludes that these reactions have significant implications for the synthesis of heterocyclic compounds and warrants further investigation for their applications in organic synthesis.
10.1002/chem.200800510
The research focuses on metal-free and PdII-promoted [2+3] cycloadditions of a cyclic nitrone to phthalonitriles, leading to the synthesis of oxadiazolines, phthalamide-PdII complexes, and dihydropyrrolyl-iminoisoindolinone-PdII complexes. These compounds were characterized using IR, 1H, and 13C NMR spectroscopy, ESI MS or FAB+ MS, elemental analyses, and X-ray diffraction analysis. The study also explores the high catalytic activity of these complexes in Suzuki-Miyaura cross-coupling reactions. The experiments involved heating mixtures of phthalonitriles and a cyclic nitrone in a sealed tube, and in some cases, the presence of palladium(II) chloride was used to facilitate the reaction. The reactants included various substituted phthalonitriles and a cyclic nitrone, while the analyses were employed to confirm the structures and properties of the synthesized compounds.