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7423620 
Journal Article 
Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations 
Ju, M; Weatherly, CD; Guzei, IA; Schomaker, JM; , 
2017 
Yes 
Angewandte Chemie (International Edition)
ISSN: 1433-7851
EISSN: 1521-3773 
WILEY-V C H VERLAG GMBH 
WEINHEIM 
56 
33 
9944-9948 
English 
28614622 
WOS:000406798700056 
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. 
amines; aziridines; nitrenes; reaction mechanisms; silver; Amines; Catalysis; Enantioselectivity; Absolute stereochemistry; Aziridines; Chemo-selectivity; Nitrenes; Nucleophilic ring opening; Reaction mechanism; Stereochemical models; Transfer reaction; Silver 
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