166107-30-8Relevant academic research and scientific papers
Catalytic kinetic resolution of cyclic secondary amines
Binanzer, Michael,Hsieh, Sheng-Ying,Bode, Jeffrey W.
supporting information; experimental part, p. 19698 - 19701 (2012/01/13)
The catalytic resolution of racemic cyclic amines has been achieved by an enantioselective amidation reaction featuring an achiral N-heterocyclic carbene catalyst and a new chiral hydroxamic acid cocatalyst working in concert. The reactions proceed at room temperature, do not generate nonvolatile byproducts, and provide enantioenriched amines by aqueous extraction.
Room temperature palladium-catalyzed intramolecular hydroamination of unactivated alkenes
Michael, Forrest E.,Cochran, Brian M.
, p. 4246 - 4247 (2007/10/03)
A mild and facile Pd-catalyzed intramolecular hydroamination of unactivated alkenes is described. This reaction takes place at room temperature and is tolerant of synthetically useful acid-sensitive functional groups. The formation of hydroamination products rather than oxidative amination products is due to the use of a tridentate ligand on Pd which effectively inhibits β-hydride elimination. Copyright
New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction
Occhiato, Ernesto G.,Prandi, Cristina,Ferrali, Alessandro,Guarna, Antonio,Venturello, Paolo
, p. 9728 - 9741 (2007/10/03)
The Pd-catalyzed coupling reaction of lactam or lactone-derived vinyl triflates and phosphates with α-alkoxydienylboronates gives conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety. If subjected to mild acidic hydrolysis, these compounds undergo a 4π electrocyclization process (Nazarov reaction) which furnishes cyclopenta-fused O- and N-heterocycles in good yields. The scope of the work has been that of closely examining the role and effect of both the heteroatom and the heterocycle ring size on the outcome of the electrocyclization, as well as the torquoselectivity of this process. The presence of the heteroatom was essential in stabilizing the oxyallyl cation intermediate, thus allowing the reaction to occur. The ring size was also a basic parameter in the cyclization step: five-membered azacycles required more drastic conditions to give 5-5 fused systems and did so only after an initial hydrolysis to the corresponding divinyl ketones. As for the torquoselectivity, with both 2-methyl and 4-methyl substituted lactam derivatives steric interactions seem to have a role in forcing the conrotatory process to take place in one sense only: allowing the synthesis of diastereomerically pure compounds to be realized. Because different patterns of substitution on the heterocycle are compatible with the reaction conditions, the methodology developed could be very useful for the synthesis of natural products and biologically active compounds containing cyclopenta-fused O- and N-heterocycle moieties.
The Cyclization of Hex-5-enylcarbamates and Related Compounds with Benzeneselenyl chloride and Some Reactions of the 2-Substituted Piperidine Products
Morella, Angelo M.,Ward, A. David
, p. 445 - 468 (2007/10/02)
The reaction of hex-5-enylcarbamates with benzeneselenyl chloride gives adducts which cyclize in the presence of silica or stannic chloride, to 2-phenylselenomethylpiperidine derivatives which are unstable, both thermally and on silica.The selenoxides also undergo a Pummerer-type reaction to form 2-acetoxy(phenylseleno)methylpiperidine systems which can be oxidatively converted into a piperidine 2-aldehyde.The selenoxides react with carbon tetrachloride in base to form a 2,2,2-trichloroethyl substituent.Both the selenoxides and the phenylseleno groups of the cyclized products can be displaced by nucleophiles.Ethy hept-6-enylcarbamate did not give a cyclic product with benzeneselenyl chloride and silica, and gave a poor yield of a hexahydroazepine with stannic chloride.Hex-5-enamide cyclized to give a lactone, rather than a lactam, product.Hex-5-enenitrile gave Ritter reaction products with benzeneselenyl chloride in acetonitrile, and a dimer in non-nucleophilic solvents.
