Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 2, Pages 391-404Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100858
Keywords
Aziridines; Epoxides; Hydroperoxylation; 3-Hydroperoxy oxindoles; Hydroperoxy amines; Hydroperoxy alcohols
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Funding
- SERB, New Delhi [CRG/2020/000650, EMR/2016/001161]
- UGC, New Delhi
- CSIR, New Delhi
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The catalyst and organic solvent-free regioselective hydroperoxylation method allows for the synthesis of secondary benzylic beta-hydroperoxy amines and alcohols, as well as tertiary 3-hydroperoxy oxindoles, and is also applicable to less reactive alkyl aziridines. Additionally, an acid-catalyzed Kornblum-DeLaMare type rearrangement of secondary benzylic hydroperoxide has been discovered to produce amino- and hydroxyl ketones.
A catalyst and organic solvent-free regioselective hydroperoxylation of aziridines and epoxides, including spiroaziridine- and spiroepoxy oxindoles have been explored with commercially available 50% aq. H2O2. This method provides an access to secondary benzylic beta-hydroperoxy amines and -alcohols and tertiary 3-hydroperoxy oxindoles. The protocol is also applicable to the less reactive alkyl aziridines. Furthermore, an acid-catalyzed Kornblum-DeLaMare type rearrangement of secondary benzylic hydroperoxide has also been revealed to afford amino- and hydroxyl ketones.
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