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Helical Phenanthrenes 3: Syntheses, Enrichment of Enantiomers, and Barriers to Racemization of Twisted 9, 10-Phenanthrenequinones

Fritsch, R. ; Hartmann, E. ; Andert, D. ; Mannschreck, Albrecht



Abstract

The known syntheses of the 9, 10-phenanthrenequinones 10a – c were improved by the chlorotrimethylsilane modification of the acyloin condensation of biaryl diesters. The novel quinones 4a, 4b, and 12 were prepared. For the first time, enantiomers (M and P) of this class of compounds were enriched semipreparatively by liquid chromatography on optically active sorbents. The barriers to thermal ...

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