%0 Journal Article %A Ton, Thi My Uyen %A Tejo, Ciputra %A Ling Ying Tiong, Diane %A Wai Hong Chan, Philip %D 2012 %T Copper(II) Triflate Catalyzed Amination and Aziridination of 2-Alkyl Substituted 1,3-Dicarbonyl Compounds %U https://acs.figshare.com/articles/journal_contribution/Copper_II_Triflate_Catalyzed_Amination_and_Aziridination_of_2_Alkyl_Substituted_1_3_Dicarbonyl_Compounds/2526772 %R 10.1021/ja301415k.s001 %2 https://ndownloader.figshare.com/files/4169767 %K 1.2 equiv %K adduct %K Dicarbonyl %K coordination %K allylic %K material %K substituent %K compound %K CompoundsA %K substrate %K aziridine product %K bond %K orthogonal modes %K Substituted %K Triflate %K method %K Alkyl %K divergence %K phen %K product selectivity %K formation %K Catalyzed %K iminoiodane %K alkyl %K Lewis acidic metal catalyst %K phenanthroline %K presence %K Aziridination %K reaction conditions %K aminated %K diacyl %K acyl %K aziridination %K nitrogen source %K derivative %K Cu %K PhI %K dicarbonyl %K reactivity %K Amination %K modification %K enolic form %K amination %X A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu­(OTf)2 + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhINTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic CH bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the β-aminated adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2–3 equiv was discovered to result in preferential formal aziridination of the CC bond of the 2-alkyl substituent of the starting material and formation of the aziridine product. %I ACS Publications