Role of imine isomerization in the stereocontrol of the Staudinger reaction between ketenes and imines
Fernando P. Cossío, Abel de Cózar, Miguel Á. Sierra, Luis Casarrubios, Jaime G. Muntaner, Bimal Krishna Banik, Debasish Bandyopadhyay
Abstract
isomerization patterns of the imine. The second step consists of a conrotatory electrocyclization of the zwitterionic intermediate formed in the previous step. This latter pericyclic step depends on the inward/outward torquoelectronic effects generated by the substituents of the imine. The impact of these factors on the stereochemistry of this reaction has been analyzed kinetically by numerical methods. The results of these simulations are compatible with the experimental results and support these conclusions.
Topics & Concepts
ImineIsomerizationPericyclic reactionChemistryConrotatory and disrotatoryNucleophileNucleophilic additionCarbon atomComputational chemistryKeteneStaudinger reactionKeteniminePhotochemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalysisRing (chemistry)Synthesis of β-Lactam CompoundsChemical Synthesis and AnalysisAsymmetric Hydrogenation and Catalysis