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Copper(II) Triflate Catalyzed Amination and Aziridination of 2-Alkyl Substituted 1,3-Dicarbonyl Compounds
journal contribution
posted on 2012-05-02, 00:00 authored by Thi My
Uyen Ton, Ciputra Tejo, Diane Ling Ying Tiong, Philip Wai Hong ChanA 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 PhINTs 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 CH 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 CC bond of the 2-alkyl substituent
of the starting material and formation of the aziridine product.
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Keywords
1.2 equivadductDicarbonylcoordinationallylicmaterialsubstituentcompoundCompoundsAsubstrateaziridine productbondorthogonal modesSubstitutedTriflatemethodAlkyldivergencephenproduct selectivityformationCatalyzediminoiodanealkylLewis acidic metal catalystphenanthrolinepresenceAziridinationreaction conditionsaminateddiacylacylaziridinationnitrogen sourcederivativeCuPhIdicarbonylreactivityAminationmodificationenolic formamination
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