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

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 si...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2015-10, Vol.6 (10), p.6008-6012
Main Authors: Li, Bao-Sheng, Wang, Yuhuang, Jin, Zhichao, Chi, Yonggui Robin
Format: Article
Language:English
Subjects:
Bonding
Breaking
Carbon-carbon composites
Catalysis
Catalysts
Chemistry
Heterocyclic compounds
Imines
Transition metals
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Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc01972a