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Synthesis 2001(12): 1856-1860
DOI: 10.1055/s-2001-17520
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Chiral Macrocyclic Di-imines Containing Tetrapyrrole and Tripyrrane Subunits

Kerstin Gunst, Stephan Seggewies, Eberhard Breitmaier*
Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
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Publication History

Received 26 February 2001
Publication Date:
11 August 2004 (online)

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Abstract

There were five cyclic expanded porphyrinogen-like di-imines, 3a,b, 5a,b and 10a synthesized from tri- and tetrapyrrolic dialdehydes 1, 4 and 9 and (R)-(+)- and (S)-(-)-1,1"-binaphthyl-2,2"-diamine 2a and 2b, respectively. In these nonaromatic macrocycles the chiral atropisomeric 1,1"-binaphthyl substructure is part of the ring system.

Key words

macrocycles - Schiff bases - imines - cyclization - chirality

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Forcefield investigations were performed by using SYBYL force field by Tripos, Inc., implemented in PC Spartan Program,Wavefunction, Inc.