Oxazolidinones constitute an important class of biologically relevant organic molecules that have also been used as chiral ligands and pharmaceutical precursors.  Prior work from our group revealed an efficient strategy to synthesize oxazolidinones from the direct coupling of 2-substituted aziridine and CO2 in the presence of a (salen)CrIII catalyst.  Surprisingly, in absence of an added cocatalyst such as dimethylaminopyridine (DMAP), the reaction exhibited excellent selectivity favoring 5-substituted oxazolidinones over its 4-substituted isomers.  In this presentation we attempt to delineate the origin of this selectivity through a combined experimental and theoretical investigation for the mechanism of this reaction.

Origin of selectivity in the formation of substituted oxazolidinones from the (salen)Cr-catalyzed [Aziridine + CO<sub>2</sub>] coupling: A combined experimental and theoretical study

244th National Meeting (2012)

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Origin of selectivity in the formation of substituted oxazolidinones from the (salen)Cr-catalyzed [Aziridine + CO2] coupling: A combined experimental and theoretical study

Origin of selectivity in the formation of substituted oxazolidinones from the (salen)Cr-catalyzed [Aziridine + CO₂] coupling: A combined experimental and theoretical study