Volume 38, Issue 24 pp. 3650-3653
Communication

“Figure Eight” Cyclooctapyrroles: Enantiomeric Separation and Determination of the Absolute Configuration of a Binuclear Metal Complex

Andreas Werner†

Andreas Werner†

Institut für Organische Chemie der Universität, Währinger Strasse 38, A-1090 Wien (Austria)

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Martin Michels

Martin Michels

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

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Lars Zander

Lars Zander

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

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Johann Lex

Johann Lex

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

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Emanuel Vogel

Emanuel Vogel

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

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Abstract

The hypothesized racemate separation of cyclooctapyrroles with chiral figure eight conformations—and of metal complexes derived from these ligands—has been realized. The cyclooctapyrrole 1 (as hexadecaethyl derivative), which according to NMR analysis exhibits restricted mobility, and its binuclear palladium and copper complexes could be separated into stable enantiomers by preparative chromatography on a chiral phase. In the case of the palladium complex and the free ligand 1 it was also possible to determine the absolute configuration of the enantiomers.

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