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Issue 35, 2018
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Different hybridized oxygen atoms controlled chemoselective formation of oxocarbenium ions: synthesis of chiral heterocyclic compounds

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Abstract

Based on the electronic properties of different hybridized oxygen atoms (sp3versus sp2) in the structure of O,O-acetals containing an enol ether moiety, the chemoselective formation of oxocarbenium ions was realized to furnish diversified chiral heterocyclic compounds with excellent stereoselectivities by reacting with different types of nucleophiles. Additionally, an unexpected intramolecular oxocarbenium ion transfer was also reported to form polycyclic products containing the O,O-acetal functional group.

Graphical abstract: Different hybridized oxygen atoms controlled chemoselective formation of oxocarbenium ions: synthesis of chiral heterocyclic compounds

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Publication details

The article was received on 20 Jul 2018, accepted on 20 Aug 2018 and first published on 21 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01743C
Citation: Org. Biomol. Chem., 2018,16, 6507-6520
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    Different hybridized oxygen atoms controlled chemoselective formation of oxocarbenium ions: synthesis of chiral heterocyclic compounds

    X. Wu, Z. You and Y. Liu, Org. Biomol. Chem., 2018, 16, 6507
    DOI: 10.1039/C8OB01743C

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