Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 15, Pages 7796-7805Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00830
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [FOR 1296]
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An NHC-catalyzed nitro-Stetter/elimination/Stetter reaction sequence employs nitroalkenes as latent 1,2-dication synthons providing a novel access to highly useful symmetrical and unsymmetrical 2-aryl substituted 1,4-diketone building blocks from commercially available aldehyde precursors. For less activated (aliphatic) aldehydes, a cooperative catalytic strategy has been developed via the merger of NHC and H-bonding catalysis. To further showcase the versatility of our approach, a great variety of these unprecedented 1,4-diketones are used to efficiently synthesize polysubstituted pyrroles-including those with hetaryl substituents in good to excellent yields in a multicatalytic metal-free, four-step one-pot cascade reaction under mild, yet robust, conditions.
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