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Updated: Feb 14, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts
Bao-Sheng Li1, Yuhuang Wang1, Zhichao Jin1
1Division of Chemistry & Biological Chemistry , School of Physical & Mathematical Sciences , Nanyang Technological University , Singapore , 637371 , Singapore .
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.
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