65113-00-0Relevant academic research and scientific papers
Entropy versus tether strain effects on rates of intramolecular 1,3-dipolar cycloadditions of N-alkenylnitrones
Krenske, Elizabeth H.,Houk,Holmes, Andrew B.,Thompson, John
, p. 2181 - 2184 (2011)
Intramolecular 1,3-dipolar cycloadditions of two N-alkenylnitrones are studied by means of density functional theory calculations. Cycloaddition of an acyclic 4-hexenylnitrone led to the expected isoxazolidine in 46% yield, but a 4-cycloheptenylnitrone did not react. Calculations of the transition states for cycloaddition indicate that although the cycloheptenyl nitrone has a more favorable activation entropy, the strain associated with distortion of the tethering groups into the required boat conformation disfavors the reaction of the cyclic substrate over the acyclic substrate by 8.7 kcal/mol.
A formal total synthesis of (±)-ferruginine by Pd-catalyzed intramolecular aminocarbonylation
Ham, Won-Hun,Jung, Young Boon,Lee, Kyunghae,Oh, Chang-Young,Lee, Kee-Young
, p. 3247 - 3248 (2007/10/03)
A practical and efficient synthetic route to the neuroactive alkaloid ferruginine has been developed. 8-Azabicyclo[3.2.1]octane skeleton 4 was prepared in one step by intramolecular aminocarbonylation of 3 catalyzed by palladium.
