An Approach to α‐ and β‐Amino Peroxides via Lewis Acid Catalyzed Ring Opening‐Peroxidation of Donor‐Acceptor Aziridines andN‐Activated Aziridines

Abstract

Site-selective ring-opening process of two different aziridine classes with hydroperoxide is described herein that provides access to various α-and β-amino and α-(imino)-peroxy compounds. This strainrelease-driven peroxide addition to aziridines represents an alternative approach for entries to biologically significant heteroatom substituted organic peroxides and complements existing methods in the field. The peroxide products obtained by this method displayed a different reactivity during peroxide-specific rearrangement processes promoted by either acid or base. Mechanistic studies and useful synthetic elaboration of the products have also been presented.

Access to 3,3′-disubstituted peroxyoxindole derivatives and α-peroxyamides via azaoxyallyl cation-guided addition of hydroperoxides

“…In line with our continued interest in developing a new strategy for peroxy-containing compounds, 14 we herein disclose a transition metal-free, azaoxyallyl cation-guided, mild and operationally simple strategy that allows the synthesis of various 3,3′-peroxyoxindoles and α-peroxyamides.…”

Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides

“…The reaction can be scaled up to the grams in 70% yield. The use of the H 2 O 2 or TBHP/Sc(OTf) 3 system for ring opening of donor-acceptor aziridines 92 leads to α-sulfanilamido peroxides 93 and 94 in good yield (Scheme 33) [126]. The reaction can be scaled up to the grams in 70% yield.…”

“…Such a Lewis acid as Cu(OTf)2 turned out to be the most effective catalyst for the synthesis of peroxides 162 by the ring opening reaction of activated aziridines 160 under the action of various hydroperoxides 161. It was found that electron-neutral or halogenated substrates 160 provide better results in comparison with substrates containing electron-withdrawing substituents in an aromatic ring (Scheme 56) [126]. Such a Lewis acid as Cu(OTf) 2 turned out to be the most effective catalyst for the synthesis of peroxides 162 by the ring opening reaction of activated aziridines 160 under the action of various hydroperoxides 161.…”

“…Such a Lewis acid as Cu(OTf) 2 turned out to be the most effective catalyst for the synthesis of peroxides 162 by the ring opening reaction of activated aziridines 160 under the action of various hydroperoxides 161. It was found that electron-neutral or halogenated substrates 160 provide better results in comparison with substrates containing electronwithdrawing substituents in an aromatic ring (Scheme 56) [126].…”

Nanomaterials for miRNA detection: the hybridization chain reaction strategy

“…metal-based nanomaterials (nanoparticles, nanorods, nanosheets, nanowires, nanoflares, nanotags, and nanoclusters) provides a suitable platform for miRNAs recognition 40,41 . Moreover, the two hairpin probes in miRNAs showed interaction resulting in the signal changes owed to HCR.…”