99893-05-7Relevant articles and documents
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
, p. 4124 - 4127 (2011)
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.