Iron(III)-Mediated Bicyclization of 1,2-Allenyl Aryl
Ketones: Assembly of Indanone-Fused Polycyclic Scaffolds and Dibenzo[a,e]pentalene Derivatives
Posted on 2019-07-11 - 21:14
The
rapid construction of three-dimensional fused carbocycles is
a key challenge in synthetic chemistry. Herein, an unprecedented and
practical tandem Nazarov/oxidative umpolung 4π-ring closure
of readily available 1,2-allenyl aryl ketones mediated by iron(III)
chloride has been developed, furnishing a new family of indanone-fused
molecular architectures in moderate to excellent yields. The indanone-containing
blocks can be efficiently converted to unsymmetrical dibenzo[a,e]pentalenes. Significantly, divergent
synthetic applications have been achieved to provide densely functionalized
polycyclic arrays.
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Miao, Maozhong; Jin, Mengchao; Chen, Panpan; Wang, Lei; Zhang, Shouzhi; Ren, Hongjun (2019). Iron(III)-Mediated Bicyclization of 1,2-Allenyl Aryl
Ketones: Assembly of Indanone-Fused Polycyclic Scaffolds and Dibenzo[a,e]pentalene Derivatives. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b02079
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AUTHORS (6)
MM
Maozhong Miao
MJ
Mengchao Jin
PC
Panpan Chen
LW
Lei Wang
SZ
Shouzhi Zhang
HR
Hongjun Ren
CATEGORIES
- Biophysics
- Biochemistry
- Space Science
- Physical Sciences not elsewhere classified
- Microbiology
- Genetics
- Molecular Biology
- Neuroscience
- Physiology
- Biotechnology
- Environmental Sciences not elsewhere classified
- Chemical Sciences not elsewhere classified
- Ecology
- Biological Sciences not elsewhere classified
- Infectious Diseases
KEYWORDS
indanone-fusedunsymmetricalumpolungAllenyldibenzoHereinfurnishingIndanone-Fused Polycyclic Scaffoldsfunctionalized polycyclic arraysAssemblyBicyclizationNazarovallenylindanone-containing blocks4π-chloridepentalene DerivativesarylyieldconstructionArylapplicationclosurechallengeKetoneDibenzocarbocycleketonetandem