期刊
CHEMICAL SCIENCE
卷 6, 期 10, 页码 6008-6012出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc01972a
关键词
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资金
- Singapore National Research Foundation
- Ministry of Education
- Nanyang Technological University (NTU)
- China's Thousand Talent Plan
- National Natural Science Foundation of China [21132003, 21472028]
- Guizhou University
The addition of an organic catalyst to the ketone moiety of a gamma-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 alpha-carbon selective reactions with azomethine imines to afford nitrogen-containing heterocyclic compounds with excellent diastereo-and enantioselectivities. 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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