期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 22, 页码 4876-4882出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500600
关键词
Synthetic methods; Electrochemistry; Polycycles; Chiral resolution; Propellanes; Vibrational circular dichroism; Density functional calculations
资金
- BASF SE
- Kompetenzzentrum der Integrierten Naturstoff-Forschung (Johannes Gutenberg University Mainz, Germany)
- Deutsche Forschungsgemeinschaft (DFG) (Chemistry at Spin Centers) [SFB 813]
The anodic treatment of 2,4-dimethylphenol offers a powerful and direct method for the construction of a dehydrotetramer with four contiguous stereocentres on a multigram scale. The installation of propellanes on this scaffold using enantiomerically pure carbonyl compounds leads to a mixture of diastereomers. This mixture is easily separable using standard chromatography and gives rise to optically pure cyclopenta-[b]benzofurans which are important scaffolds in a variety of natural products. The synthesis is easy to perform and allows a reliable access to chiral compounds with very high enantiomeric excess. It was possible to determine the absolute configuration of these compounds by comparison of experimentally recorded and calculated VCD spectra of all enantiomers.
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