Our lab recently disclosed a highly diastereoselective kinetic resolution of unsaturated amides in a chlorocyclization reaction.1Key to the success of the transformation was the different H-bonding affinities of the two enantiomers to the protonated chiral catalyst. Our efforts to extend this chemistry to the kinetic resolution of propargyl amides in an analogous fashion will be presented in this poster.  With face-selectivity not being an issue in alkyne halofunctionalization, the kinetic resolution will exclusively depend on the interactions between the two enantiomers of the racemate and the chiral catalyst.1. Jaganathan, A.; Staples, R. J.; Borhan, B. J. Am. Chem. Soc. 2013  , 135, 14806-14813.

Kinetic resolution of propargyl amides via chlorocyclization

248th National Meeting (2014)

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