Aziridines are of significant importance as intermediates for the synthesis of nitrogen-containing molecules. We will present a boron-catalyzed kinetic resolution that produces enantioenriched terminal aziridines.  Synthetically useful enantiomeric excess values of > 99%and s-values ranging from 32-236 are observed with a range of substrates. The chiral modifier can be cleaved from the byproduct and isolated in excellent yield.  The utility of the resolved aziridines is demonstrated through several stereoselective transformations to provide access to functionalized small molecules.

Kinetic resolution of N-acylaziridines

243rd National Meeting (2012)

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