2646-33-5Relevant academic research and scientific papers
Studies Targeting Ryanodol Result in an Annulation Reaction for the Synthesis of a Variety of Fused Carbocycles
Karmakar, Rajdip,Rheingold, Arnold L.,Micalizio, Glenn C.
supporting information, p. 6126 - 6129 (2019/08/26)
An annulation reaction is described to access a range of polycyclic and highly oxygenated carbocycles. First developed in an approach to the synthesis of ryanodol, metallacycle-mediated annulative diketone-alkyne coupling defines a framework for realization of new retrosynthetic relationships for complex molecule synthesis. In addition to demonstrating this reaction in the context of forging distinct carbocyclic systems, including those featuring a seven-membered ring, the choice of quenching reagent leads to unique reaction outcomes.
1,3-dipolar cycloaddition of hydrazones with α-oxo-ketenes: A three-component stereoselective entry to pyrazolidinones and an original class of spirooxindoles
Presset, Marc,Mohanan, Kishor,Hamann, Marie,Coquerel, Yoann,Rodriguez, Jean
supporting information; experimental part, p. 4124 - 4127 (2011/10/04)
Stereodefined monocyclic, spirobicyclic, and bis-spirotricyclic pyrazolidin-3-ones can be prepared efficiently by a three-component reaction involving a 1,3-dipolar cycloaddition of azomethine imines obtained from hydrazones with α-oxo-ketene dipolarophiles generated in situ. The reaction allows the creation of four covalent bonds and two contiguous chiral quaternary centers with excellent diastereoselectivity in a single catalyst/additive-free, highly atom-economical transformation. From a fundamental point of view, the reaction introduces α-oxo-ketenes as effective dipolarophiles in 1,3-dipolar cycloadditions.
