Chemo‐ and Enantioselective Intramolecular Silver‐Catalyzed Aziridinations

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  • Minsoo Ju
    Department of Chemistry University of Wisconsin-Madison 1101 University Avenue Madison WI 53706 USA
  • Cale D. Weatherly
    Department of Chemistry University of Wisconsin-Madison 1101 University Avenue Madison WI 53706 USA
  • Ilia A. Guzei
    Department of Chemistry University of Wisconsin-Madison 1101 University Avenue Madison WI 53706 USA
  • Jennifer M. Schomaker
    Department of Chemistry University of Wisconsin-Madison 1101 University Avenue Madison WI 53706 USA

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<jats:title>Abstract</jats:title><jats:p>Asymmetric nitrene‐transfer reactions are a powerful tool for the preparation of enantioenriched amine building blocks. Reported herein are chemo‐ and enantioselective silver‐catalyzed aminations which transform di‐ and trisubstituted homoallylic carbamates into [4.1.0]‐carbamate‐tethered aziridines in good yields and with ee values of up to 92 %. The effects of the substrate, silver counteranion, ligand, solvent, and temperature on both the chemoselectivity and ee value were explored. Stereochemical models were proposed to rationalize the observed absolute stereochemistry of the aziridines, which undergo nucleophilic ring opening to yield enantioenriched amines with no erosion in stereochemical integrity.</jats:p>

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