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Synthesis and Isolation of Enantiomerically Enriched Cyclopenta[ b ]benzofurans Based on Products from Anodic Oxidation of 2,4‐Dimethylphenol
Author(s) -
Mirion Michael,
Andernach Lars,
Stobe Caroline,
Barjau Joaquin,
Schollmeyer Dieter,
Opatz Till,
Lützen Arne,
Waldvogel Siegfried R.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500600
Subject(s) - chemistry , diastereomer , enantiomer , absolute configuration , organic chemistry , combinatorial chemistry
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.