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Jennifer Cockrell, Christopher Wilhelmsen, Heather Rubin, Allen Martin and Prof. Jeremy B. Morgan Enantioselective Synthesis and Stereoselective Ring Opening of N-Acylaziridines Angewandte Chemie International Edition 51

Version of Record online: 3 SEP 2012 | DOI: 10.1002/anie.201204224

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Kinetic resolution of N-acylaziridines by nucleophilic ring opening was achieved with (R)-BINOL as the chiral modifier under boron-catalyzed conditions (see scheme; Ar=3,5-dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2-chloroamide with recovery of (R)-BINOL.

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