Michael reaction on example of unsaturated ketones of bicyclo[3.3.1]nonane series

Synthesis of an Orthogonal Topological Analogue of Helicene

“…[12a] By selection of the aromatic spacer and the number of BCN units, the synthetic strategy towards 1 allows for the control of important properties of the resultant tubular structure, such as diameter and length. Furthermore, the key building block in our synthesis, bicyclo-A C H T U N G T R E N N U N G [3.3.1]nonane-2,6-dione (2), can be regiospecifically and stereoA C H T U N G T R E N N U N G selectively functionalized [14] in advance, which allows for the introduction of substituents to improve, for instance, solubility. Additionally, the aromatic skeleton is parallel to the axis of propagation, which creates a solvophobic cavity inside the molecule and makes 1 a potential host for different guests based on p-p [13] or cation-p [15] interactions.…”

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics

“…Smirnov and coworkers investigated the addition of diethylmalonate and mononitroalkanes several years ago. 330 Following their report, Zavarzin's group demonstrated a similar approach employing polynitroalkanes. 331 As expected, the more reactive dinitro and trinitroalkane Michael donors (693, 694) reacts with enone 692 at a much faster rate to form bicyclo[3.3.1]nonane-containing nitroalkanes (695, 696) in high yields (Scheme 157).…”

“…It was also found that much higher temperature (90 °C) and a high boiling solvent (Bu t OH) is required to construct the double condensed product (700) of nitroform and diene-dione 697 (Scheme 159). 330,331 4.4.5.3 Amination reaction. Palladium-catalyzed amination reactions in the bicyclo[3.3.1]nonane series is widely investigated by Renard and coworkers.…”

“…It was also found that much higher temperature (90 °C) and a high boiling solvent (Bu t OH) is required to construct the double condensed product (700) of nitroform and diene-dione 697 (Scheme 159). 330,331 4.4. aminoquinolines exhibit interesting pharmacological properstudies on the synthesis of similar analogues have received much attention in recent years. Renard's team, through a thorough screening of solvents, bases, ligands, and Pd-catalysts, found that haloquinolino-bicyclo[3.3.1]nonanes 701 could be converted into corresponding aminoquinolines 702 using Pd 2 (dba) 3 as the catalyst, BINAP as the ligand, cesium carbonate as the base, and dioxane as the solvent with high yields.…”