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Issue 10, 2015
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Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts

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Abstract

The addition of an organic catalyst to the ketone moiety of a γ-mono-chloride substituted cyclobutenone destroys its stable, conjugated and nearly planar structure. The C–C bond in the resulting less stable anionic oxy-substituted non-planar intermediate is then activated. The breaking of one C–C single bond leads to a catalyst-bound intermediate that undergoes α-carbon selective reactions with azomethine imines to afford nitrogen-containing heterocyclic compounds with excellent diastereo- and enantio-selectivities. Our organocatalytic approach provides a new reaction pattern for C–C bond activation of cyclobutenones that is unavailable with transition metal catalysis. In addition, the present study with isothioureas as the organocatalysts expands the potential in using organocatalysts for C–C bond breaking and selective reactions.

Graphical abstract: Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts

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Publication details

The article was received on 02 Jun 2015, accepted on 18 Jul 2015 and first published on 20 Jul 2015


Article type: Edge Article
DOI: 10.1039/C5SC01972A
Chem. Sci., 2015,6, 6008-6012
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts

    B. Li, Y. Wang, Z. Jin and Y. R. Chi, Chem. Sci., 2015, 6, 6008
    DOI: 10.1039/C5SC01972A

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