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Communication | Special issue | Vol 58, No. 1, 2002, pp.137-146
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S(M)61
Studies on a Chirality of Orellanine. Spectral Nonequivalence of Atropisomers of Tetra-O-methylorellanine and Related Compounds Induced by Chiral Solvating Agents

Róza Antkowiak, Wieslaw Z. Antkowiak,* and Barbara Nowak-Wydra

*Facluty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznan, Poland

Abstract

The precise carbon-hydrogen correlations of orellanine tetramethyl ether were established by NMR techniques and the methylated alkaloid, as well as some of its structural analogues, was subjected to 1H NMR experiments with the use of (R)-(+)-t-butylphenylphosphinothioic acid, BINOL or TADDOL as the chiral solvating agents. It was found that tetramethylorellanine, as well as 3,3’-dimethoxy-2,2’-bipyridine-N,N’-dioxide, and some other model compounds gave, in such conditions, proton spectra being composed of separated patterns, each of which corresponds to the individual enantiomer.