Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 40, Pages 11835-11838Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506232
Keywords
arenes; aromaticity; fused-ring systems; synthetic methods; X-ray diffraction
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Funding
- FCI (Sachkostenzuschuss)
- DFG [SFB 749]
- DFG (Emmy-Noether Program)
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Described is the development of a highly efficient 2 pi disrotatory ring-opening aromatization sequence using bicyclo[3.1.0]hexan-2-ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively, is achieved. Additionally, the utility of this method was demonstrated in a short synthesis of sekikaic acid methyl ester.
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